Reaction #565237

Reaction equation

Sodium

cyclopropylcarboxamidine hydrochloride

acetic acid

ethyl 3-oxotetrahydrothiopyran-2-carboxylate

→

title compound

Yield 81.5%

2-Cyclopropyl-7,8-dihydro-4-hydroxy-6H-thiopyrano[3,2-d]pyrimidine

Yield 81.5%

Solvents

methanol

Conditions

Workup

1. 1
   workup.WAITfollowed after 1/4 hour

Procedure

Sodium metal (3.94 g, 0.17 g atom) was dissolved in methanol (150 ml) and cyclopropylcarboxamidine hydrochloride (21.0 g, 0.174 mol) was added followed after 1/4 hour stirring by the addition of ethyl 3-oxotetrahydrothiopyran-2-carboxylate (27.2 g, 0.145 mol). The reaction mixture was stirred at 25° C. for 18 hours then treated with ice water (200 ml) and neutralized with acetic acid to give 24.6 g of the title compound which melted at 249°-250° C.

Source