Phosphorus oxychloride → 4-Chloro-5,7-dihydrothieno[3,4-d]pyrimidine

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Reaction Steps

To a solution of the 5,7-dihydrothieno[3,4-d]pyrimidin-4-ol (0.50 g, 3.2 mmol) in DCE (50 mL) was added DIEA (0.42 g, 3.2 mmol) and POCl3 (1.5 g, 9.8 mmol). The mix was refluxed overnight. After cooling, the solvent was removed and the residue was subject to silica gel chromatography, eluting with hexane/ethyl acetate (4:1) to give 4-chloro-5,7-dihydrothieno[3,4-d]pyrimidine (0.45 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 8.84 (s, 1H), 4.37 (s, 2H), 4.27 (s, 2H).

Provenance & Evidence