GB699812A - Manufacture of substituted pyrimidones - Google Patents
Manufacture of substituted pyrimidonesInfo
- Publication number
- GB699812A GB699812A GB2915850A GB2915850A GB699812A GB 699812 A GB699812 A GB 699812A GB 2915850 A GB2915850 A GB 2915850A GB 2915850 A GB2915850 A GB 2915850A GB 699812 A GB699812 A GB 699812A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidone
- diketene
- methyl
- dimethyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000008318 pyrimidones Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 9
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 alkyl radical Chemical class 0.000 abstract 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- VJQCNCOGZPSOQZ-UHFFFAOYSA-N 1-Methylguanidine hydrochloride Chemical compound [Cl-].C[NH2+]C(N)=N VJQCNCOGZPSOQZ-UHFFFAOYSA-N 0.000 abstract 1
- DSJVSLJDQPTJSK-UHFFFAOYSA-N 1-methyl-1-phenylguanidine Chemical compound NC(=N)N(C)C1=CC=CC=C1 DSJVSLJDQPTJSK-UHFFFAOYSA-N 0.000 abstract 1
- KWXIPEYKZKIAKR-UHFFFAOYSA-N 2-amino-4-hydroxy-6-methylpyrimidine Chemical compound CC1=CC(O)=NC(N)=N1 KWXIPEYKZKIAKR-UHFFFAOYSA-N 0.000 abstract 1
- USHZYUPZIKQYMI-UHFFFAOYSA-N 2-methylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C(N)=N USHZYUPZIKQYMI-UHFFFAOYSA-N 0.000 abstract 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 abstract 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 abstract 1
- OCOHPSHRDKBGOZ-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C=C(C)N1 OCOHPSHRDKBGOZ-UHFFFAOYSA-N 0.000 abstract 1
- GPFHJDDZKIADGL-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-3-phenylpyrimidin-4-one Chemical compound CSC1=NC(C)=CC(=O)N1C1=CC=CC=C1 GPFHJDDZKIADGL-UHFFFAOYSA-N 0.000 abstract 1
- BQXCSFIZYMLIAU-UHFFFAOYSA-N 6-methyl-2-phenyl-1h-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1C1=CC=CC=C1 BQXCSFIZYMLIAU-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001409 amidines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 abstract 1
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 abstract 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 abstract 1
- WLZHMAWFACZFSM-UHFFFAOYSA-N ethyl n'-methylcarbamimidothioate Chemical compound CCSC(N)=NC WLZHMAWFACZFSM-UHFFFAOYSA-N 0.000 abstract 1
- 229960004198 guanidine Drugs 0.000 abstract 1
- 229960000789 guanidine hydrochloride Drugs 0.000 abstract 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- NROPRCUPBJFONT-UHFFFAOYSA-N methyl n'-phenylcarbamimidothioate Chemical compound CSC(N)=NC1=CC=CC=C1 NROPRCUPBJFONT-UHFFFAOYSA-N 0.000 abstract 1
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- VFIZBHJTOHUOEK-UHFFFAOYSA-N s-ethylisothiourea Chemical compound CCSC(N)=N VFIZBHJTOHUOEK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229940035893 uracil Drugs 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Substituted pyrimidones of the general formula <FORM:0699812/IV (b)/1> (wherein R represents hydrogen or an alkyl or aryl radical, X an alkyl, aryl, -NHR1 or -SR2 group, R1 hydrogen or an alkyl radical and R2 an alkyl radical) are manufactured by reacting diketene with an amidine, guanidine or isothiourea of the general formula <FORM:0699812/IV (b)/2> or with a salt thereof if the reaction be effected in the presence of an alkaline material. The reaction is desirably carried out in a diluent medium, which should be a solvent for the second reactant, such as water, an organic solvent (e.g. an alcohol, ether, ester, ketone, aromatic hydrocarbon, or chlorinated hydrocarbon), or an aqueous organic solvent, and may take place at temperatures in the range -10 DEG to 60 DEG C. (e.g. at room temperature). When X represents -SR2, the product may be hydrolysed to the corresponding uracil and mercaptan. In examples: (1) and (2) diketene is shaken with benzamidine hydrochloride in aqueous caustic soda or with benzamidine in water to produce 2-phenyl-4-methyl-6-pyrimidone; (3) diketene is stirred with guanidine carbonate in aqueous caustic soda to yield 2-amino-4-methyl-6-pyrimidone; (4) the same product is obtained by reacting guanidine hydrochloride as in (1); (5) S-methylisothiouronium iodide (from thiourea and methyl iodide) similarly yields 2-methylmercapto-4-methyl-6-pyrimidone; (6) diketene is stirred with acetamidine hydrochloride in ethanol in the presence of sodium ethoxide to form 2 : 4-dimethyl-6-pyrimidone; (7) to (9) diketene is stirred with N-phenyl-S-methylisothiourea in ethanol, ether, chloroform, acetone, dioxan, benzene or ethyl acetate, and an intermediate product which is formed is converted with alkali to 2-methylmercapto-1-phenyl-4-methyl-6-pyrimidone; (10) diketene is stirred with N : S-dimethylisothiouronium iodide in aqueous caustic soda to given 2-methylmercapto-1 : 4-dimethyl-6-pyrimidone; (11) diketene is allowed to stand with methylguanidine hydrochloride in aqueous caustic soda to produce 1 : 4-dimethyl-2-amino-6-pyrimidone; (12) a solution of sodium in ethanol is added to a solution of methylbenzamidine hydrochloride in ethanol, the precipitated sodium chloride is removed, diketene is added and the solution allowed to stand, producing 1 : 4-dimethyl-2-phenyl-6-pyrimidone. Other starting materials specified are propionamidine, phenylacetamidine (R = H, X = C6H5CH2-), N : N1 - dimethyl - guanidine, phenylguanidine, N - methyl - N1 - phenylguanidine, S - ethylisothiourea and N - phenyl- and N-methyl-S-ethylisothiourea.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2915850A GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2915850A GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB699812A true GB699812A (en) | 1953-11-18 |
Family
ID=10287051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2915850A Expired GB699812A (en) | 1950-11-29 | 1950-11-29 | Manufacture of substituted pyrimidones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB699812A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2931887A1 (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | METHOD FOR PRODUCING 2-ALKYL OR CYCLOALKYL-4-METHYL-6-HYDROXYPYRIMIDINES |
| EP1506967A1 (en) * | 2003-08-13 | 2005-02-16 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| EP1911754A1 (en) * | 2003-08-13 | 2008-04-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7807689B2 (en) | 2004-03-15 | 2010-10-05 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
-
1950
- 1950-11-29 GB GB2915850A patent/GB699812A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2931887A1 (en) * | 1978-08-08 | 1980-02-21 | Ciba Geigy Ag | METHOD FOR PRODUCING 2-ALKYL OR CYCLOALKYL-4-METHYL-6-HYDROXYPYRIMIDINES |
| EP1506967A1 (en) * | 2003-08-13 | 2005-02-16 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| WO2005016911A1 (en) * | 2003-08-13 | 2005-02-24 | Takeda Pharmaceutical Company Limited | 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors |
| JP2005060401A (en) * | 2003-08-13 | 2005-03-10 | Syrrx Inc | Dipeptidyl peptidase inhibitor |
| EP1911754A1 (en) * | 2003-08-13 | 2008-04-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7807689B2 (en) | 2004-03-15 | 2010-10-05 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8906901B2 (en) | 2005-09-14 | 2014-12-09 | Takeda Pharmaceutical Company Limited | Administration of dipeptidyl peptidase inhibitors |
| US8222411B2 (en) | 2005-09-16 | 2012-07-17 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| US8084605B2 (en) | 2006-11-29 | 2011-12-27 | Kelly Ron C | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
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