Ammonia → 5-Chloro-2-cyclopropyl-6-(diethoxymethyl)-4-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

Ethanol (190 mL) was saturated with ammonia. 4,5-Dichloro-2-cyclopropyl-6-(diethoxymethyl)pyrimidine (i.e. the product of Example 5) (25.2 g, 86.5 mmol) was added, and the mixture sealed in a pressure vessel (Parr Instrument Co., Moline, Ill.). The mixture was warmed to 75° C., and the pressure was maintained at 40 psi (276 kPa). After 8 h at this temperature and pressure the mixture was allowed to cool to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and then filtered. The filtrate was evaporated under reduced pressure, and the residue was taken up in hexanes to crystallize the product as an off-white solid (19.97 g, 85% yield). The product recrystallized from hexanes had a melting point of 104.5-109.5° C.

Provenance & Evidence