Reaction #60793

Reaction equation

DIPEA

methyl [(6chloro-5-formylpyrimidin-4-yl)thio]acetate

intermediate 9

methyl [(6chloro-5-formylpyrimidin-4-yl)thio]acetate

→

title compound

Yield 53.9%

Methyl 4-chlorothieno[2,3-d]pyrimidine-6-carboxylate

Yield 53.9%

Solvents

cyclohexanol

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   Otherthe product purified by flash chromatography on silica eluting with hexane:diethyl ether (4:1)

Procedure

DIPEA (2.1 mL) was added to methyl [(6chloro-5-formylpyrimidin-4-yl)thio]acetate (intermediate 9) (2.9 g) in cyclohexanol (50 mL) under an inert atmosphere. The reaction mixture was heated at 120° C. for 90 minutes. The solvent was evaporated and the product purified by flash chromatography on silica eluting with hexane:diethyl ether (4:1) to afford the title compound as a pale yellow solid (1.45 g, 53%);

Source