Dimethylformamide → 2-Amino-4-chloro-6-cyano-pyrimidylacetate-t-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (17.6 g, 733 mmol) in dry N,N-dimethylformamide (DMF) at 0° C. was added dropwise t-butyl cyanoacetate (96 g, 680 mmol). The tan suspension was stirred at 0° C. for 0.5 hours then 2-amino-4,6-dichloropyrimidine (58.7 g, 358 mmol) was added batchwise. The mixture was heated slowly to 90° C. and the reaction was held at 90° C. for 18 hours. The reaction mixture was poured onto water (1 l) and the mixture was filtered. The filtrate was acidified with con HCl to pH 6 and the resultant solid was filtered and washed with water and hexanes and dried to furnish 99.64 g of the desired subject as a green powder, m.p. 107°-109° C. NMR (200 mHz) D6-acetone δ 12.8 (bs, 1 H), 8.0 (bs, 1 H), 7.8 (bs, 1 H), 6.3 (s, 1 H), 1.5 (s, 9 H).

Provenance & Evidence