GB1075295A - Improvements in or relating to the preparation of tetrahydropyrimidines - Google Patents
Improvements in or relating to the preparation of tetrahydropyrimidinesInfo
- Publication number
- GB1075295A GB1075295A GB47718/64A GB4771864A GB1075295A GB 1075295 A GB1075295 A GB 1075295A GB 47718/64 A GB47718/64 A GB 47718/64A GB 4771864 A GB4771864 A GB 4771864A GB 1075295 A GB1075295 A GB 1075295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- tetrahydropyrimidines
- acylated
- prepared
- nickel
- 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
- 150000005326 tetrahydropyrimidines Chemical class 0.000 title 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
3 - Alkyl - 2 - substituted - 3,4,5,6 - tetrahydropyrimidines in which the 2-substituent is an alkyl group or aryl hydrocarbon group, optionally substituted by halogen, are prepared by heating an acylated-N-alkyl-1,3-propane diamine in the presence of a catalyst consisting of nickel, copper, cobalt, manganese, platinum or palladium or salts thereof and in the presence of a strong base at a temperature in the range 180-200 DEG C. The acylated N-alkyl-1,3-propane-diamines may be prepared by reacting an N-alkyl, N-b -cyanoethylamine, having from 8 to 22 carbon atoms, with an acylating agent derived from a carboxylic acid and hydrogenating the product over a nickel catalyst under superatmospheric pressure and in the presence of a base.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32819463A | 1963-12-05 | 1963-12-05 | |
| US610759A US3366634A (en) | 1963-12-05 | 1967-01-23 | Preparation of tetrahydropyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1075295A true GB1075295A (en) | 1967-07-12 |
Family
ID=26986264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47718/64A Expired GB1075295A (en) | 1963-12-05 | 1964-11-24 | Improvements in or relating to the preparation of tetrahydropyrimidines |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3366634A (en) |
| GB (1) | GB1075295A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4376201A (en) * | 1981-09-14 | 1983-03-08 | The Dow Chemical Company | Preparation of 2-alkylpyrimidines |
| US4999427A (en) * | 1988-05-16 | 1991-03-12 | Dowelanco | Process for the preparation of 2-alkylpyrimidines |
| US5180700A (en) * | 1991-05-13 | 1993-01-19 | Dowelanco | Regeneration and extension of lifetime of dehydrogenation catalysts used in the preparation of 2-alkylpyrimidines |
-
1964
- 1964-11-24 GB GB47718/64A patent/GB1075295A/en not_active Expired
-
1967
- 1967-01-23 US US610759A patent/US3366634A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3366634A (en) | 1968-01-30 |
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