Formaldehyde → 5-(Hydroxymethyl)uracil

HRID 342528

Reaction equation

HRID 342528 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH2:9]=[O:10].[OH-].[K+]>O>[OH:10][CH2:9][C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1174UracilHCID 14797Potassium Hydroxide

Product 1

HCID 781685-(Hydroxymethyl)uracilYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo to a volume of 20 mL
  3. customThe solids were collected
  4. customrecrystallized from water (50 mL)

Sources & evidence

ORD record
ord-e1856cadb56d4369839b50b4722dc1d2
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Linked notes

Loading…