3,4-dihydro-2H-pyran → HCID 22125057, compound

Participants

Reaction Steps

A solution of 3.5 g (7.9 mmol) of 5-(2-bromoanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine (prepared in a method analogous to that for 5-(2,6-dichloroanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine of Example 37(f) using 2-bromoaniline in place of 2,6-dichloroaniline) in 100 ml of dichloromethane was treated with 3.3 g (39 mmol) of 2,3-dihydropyran and 15 mg (0.08 mmol) of toluenesulfonic acid monohydrate and the mixture stirred at room temperature for 3 days. Subsequently 100 ml of diethyl ether and 100 ml of brine were added. The mixture was separated and the organic phase dried over magnesium sulfate, filtered and evaporated. Flash chromatography on silica gel using diethyl ether and hexane in a ratio of 1:1 as eluent afforded 2.6 g of 5-(2-bromoanilino)methyl-4-[3-(2-(tetrahydropyranyloxy)ethyl)phenyl]amino-2-methylthiopyrimidine as a yellow oil. [Mass spectrum (ESI) MH+ =529].

Provenance & Evidence