Trimethyl orthoformate → 5-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Participants

Reaction Steps

5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde was dissolved in dichloroethane with 1-methylsulfonylpiperazine hydrochloride (1.45 eq), sodium acetate (1.45 eq), and trimethylorthoformate (1.45 eq). The solution was stirred overnight. Sodium triacetoxyborohydride (1.35 eq) was added and after three hours at room temperature the reaction was quenched with saturated sodium bicarbonate solution. The aqueous was extracted with methylene chloride, dried with sodium sulfate and purified by silica gel chromatography to give 5-chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine.

Provenance & Evidence