Reaction #532069

Reaction equation

sodium hydroxide

N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine

trans 2-methyl-cyclopropanecarboxamidine hydrochloride

→

title compound

4-Methyl-5-[2-(2-methyl-cyclopropyl)-pyrimidin-4-yl]-thiazol-2-ylamine

Solvents

2-methoxyethanol

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is cooled
2. 2
   Filtrationfiltered
3. 3
   Washwashing with water

Procedure

Powdered sodium hydroxide (300 mg) is added to a solution of N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (1 g, prepared as described by S. Wang et al J. Med. Chem. 2004, 47, 1662-1675.) and cis/trans 2-methyl-cyclopropanecarboxamidine hydrochloride (0.61 g, prepared as described in WO 03/087064) in 2-methoxyethanol (3.8 ml) and the mixture heated at 125° C. for 1 hour with stirring. The reaction mixture is cooled, filtered, washing with water to give the title compound. MS: M+H 247 and M−H 245.

Source