Acetamidine monohydrochloride → 5-Bromo-2-methylpyrimidine-4-carboxylic acid

Temperature

50 °C

To a solution of acetamidine hydrochloride (6.0 g) in ethanol (20 mL) was added sodium ethoxide (20 mL of a 21% solution in ethanol) and the reaction mixture was heated at 50° C. and mucobromic acid (6.82 g) in ethanol (10 mL) was added. After stirring at 50° C. for 1 h, a further portion of sodium ethoxide (10 mL of a 21% solution in ethanol) was added and the mixture was stirred at room temperature for 16 h. The mixture was then filtered and the filtrate reduced in vacuo. The residue was then treated with 2 M aqueous hydrochloric acid (30 mL) and stirred vigorously for 30 minutes. The resulting solid was filtered, washed with water and air dried to give 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (1.46 g). This was then heated at 175° C. for 16 h. After cooling to room temperature the mixture was purified by Kugelrohr distillation to give 5-bromo-2-methyl-pyrimidine as a white solid (746 mg).

1. stirringthe mixture was stirred at room temperature for 16 h
2. filtrationThe mixture was then filtered
3. additionThe residue was then treated with 2 M aqueous hydrochloric acid (30 mL)
4. stirringstirred vigorously for 30 minutes
5. filtrationThe resulting solid was filtered
6. washwashed with water and air
7. customdried

ORD record

ord-e5d272eb43d94d6b95a89acb111758d4

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993563B2