Water → N-(2,2-Diethoxyethyl)-2-pyrimidinamine

Participants

Reaction Steps

A solution of 2-aminopyrimidine (1.9 g.) in dried dimethylformamide (8 ml.) was dropwise added to a suspension of 50% sodium hydride (1.25g.) in dried dimethylformamide (2 ml.) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature and for 2 hours at ambient temperature. Bromoacetaldehyde diethyl acetal (4.3 g.) and dried dimethylformamide (2 ml.) were added thereto, and the mixture was stirred for 2 hours and 20 minutes at ambient temperature and for 2.5 hours at 80° C. The reaction mixture was cooled to at ambient temperature and to the mixture was added water, and then the mixture was extracted 3 times with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution in turn, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residual oil was purified by column chromatography on silica gel (25 g.) using chloroform as developing solvent to give 2-pyrimidinylaminoacetaldehyde diethyl acetal (1.4 g.), oil. This oil was allowed to stand to give crystals.

Provenance & Evidence