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

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.

1. temperaturecooling
2. stirringthe mixture was stirred for 2 hours and 20 minutes at ambient temperature and for 2.5 hours at 80° C
3. temperatureThe reaction mixture was cooled to at ambient temperature and to the mixture
4. extractionthe mixture was extracted 3 times with ethyl acetate
5. washThe extract was washed with water
6. dry with materiala saturated sodium chloride aqueous solution in turn, and dried over magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe residual oil was purified by column chromatography on silica gel (25 g.)

ORD record

ord-e3c67abef8fd4af5959ee9a83059b5d6

Source dataset

uspto-grants-1978_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04096263