Sodium Thiosulfate → tert-Butyl 2-(methanesulfonyl)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

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Reaction Steps

To a solution of 6-(tert-butoxycarbonyl)-2-methylthio-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.20 g) in methylene chloride (80 ml) was added metachloroperbenzoic acid (3.37 g). After stirring for 4 hours, a 10% aqueous solution (100 ml) of sodium thiosulfate and a saturated aqueous solution (100 ml) of sodium bicarbonate were added to the reaction mixture and the mixture was separated into layers. The water layer was extracted with methylene chloride (2×50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:acetone=20:1→10:1), whereby the title compound (2.34 g) was obtained as a colorless solid.

Provenance & Evidence