Process for the synthesis of N-(3-(1H-imidazol-1-yl)phenyl-4-(substituted)-2-pyrimidinamines
US5064963A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Apr 25, 1990 |
| Grant date | Nov 12, 1991 |
| Priority date | — |
| Expiry date | Apr 25, 2010 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D409/14
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The invention provides a novel process for producing N-[3-(1H-imidazol-1-yl)phenyl]-4-(substituted)-2 pyrimidinamine compounds in which the substituent is a 2-pyridinyl, 3-pyrindinyl, 4-pyridinyl, 2-furanyl or 2-thienyl group. The process includes the steps of (1) reacting a 3-(1H-imidazol-1-yl)benzamine with cyanamide and a halogen acid while controlling the pH of the reaction between pH about 2 to abourt 3.5 and recovering a [3-(1H-imidazol-1-yl)phenyl] guanidine dihydrohalide and (2) reacting the [3-(1H-imidazol-1-yl)phenyl] guanidine dihydrohalide so recovered with an appropriately substituted 3-dimethylamino-1-(substituted)-2-propen-1-one and a base at a pH of from about 10.5 to about 11.5 and recovering the N-[3-(1H-imidazol-1-yl)phenyl-4-(substituted)-2-pyrimidamine compound so produced. The novel process provides improved yield and purity by adhering to the stated crucial pH ranges.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.