Hydrochloric Acid → HCID 14011774, compound

Participants

Reaction Conditions

Reaction Steps

A three-necked 150 ml flask fitted with a septum, a low temperature thermometer and an addition funnel was charged under nitrogen with 11.6 ml (18.6 mmol) of 1.6 M n-butyllithium. After cooling the flask to 5° C., a solution of 2.6 ml (18.6 mmol) of diisopropylamine in 20 ml dry THF was added dropwise over 5 minutes. After addition was completed, the mixture was stirred at 5° C. for 15 minutes and then cooled to -70° C. To the reaction mixture was added a solution of 1.56 g (9.3 mmol) of 2-dimethylamino-4-methyl-5-methoxypyrimidine in 20 ml dry THF over ten minutes. The reaction mixture was then stirred at -70° C. for 1.5 hour, and a solution added of 2.0 g (18.6 mmol) of ethyl chloroformate in 20 ml dry THF over five minutes. The reaction mixture was stirred at -70° C. for a half hour and then allowed to warm to -15° C. over 15 minutes. The reaction mixture was poured into 100 ml of water, the aqueous mixture brought to pH 8.5 with 1N HCl and extracted with three 25 ml portions of chloroform. The combined extracts were dried over Na2SO4, filtered and evaporated leaving an oil. Chromatography over 100 g of silica gel with hexane/ethyl acetate (9:1) yielded 47% (1.05 g) of the title compound as a colorless liquid. NMR(CDCl3) 8.0 (s, 1H), 4.19 (q, J=7 Hz, 2H), 3.75 (s, 3H), 3.65 (s, 2H), 3.05 (s, 6H), 1.1 (t, J=7 Hz, 3H).

Provenance & Evidence