Formaldehyde → 5-(Hydroxymethyl)uracil

Participants

Reaction Conditions

Reaction Steps

A mixture of uracil (9 g, 80.3 mmol), paraformaldehyde (3 g) and 0.42N potassium hydroxide (125 mL) was heated 90 hours at 50° C. The reaction mixture was diluted with water (350 mL), stirred with Dowex® 50 ion-exchange resin (30 g, H form, 100-200 mesh), filtered, concentrated in vacuo to a volume of 20 mL and refrigerated. The solids were collected and recrystallized from water (50 mL) to give 5-hydroxymethyl-2,4(1H,3H)-pyrimidinedione (9.5 g, 65.04 mmol), m.p. 260°-300° C. (dec).

Provenance & Evidence