Sodium Hydroxide → [4-(Morpholin-4-yl)pyrimidin-2-yl]methanol

Participants

Reaction Steps

A solution of boron tribromide (9.02 ml) in dichloromethane (100 ml) was added dropwise to a stirred solution of 2-methoxymethyl-4-morpholinopyrimidine (4.99 g) in dichloromethane (50 ml) at -25° under nitrogen. After 15 minutes the mixture was allowed to warm to 0°-5°, and left to stand for 2 hours at this temperature. After pouring onto ice, the pH was raised to 14 (NaOH), and the organic phase separated off. The aqueous phase was further extracted with chloroform, and the combined extracts dried (K2CO3) and stripped. The residue was triturated with ether to give 2-hydroxymethyl-4-morpholinopyrimidine (3.16 g) as a crystalline solid, m.p. 76°-8°.

Provenance & Evidence