Hydrochloric Acid → 5-(Hydroxymethyl)uracil

HRID 2211816Notes

Reaction equation

HRID 2211816 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+].Cl>O>[OH:10][CH2:9][C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1174UracilHCID 14797Potassium Hydroxide

Product 1

HCID 781685-(Hydroxymethyl)uracilYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of uracil (3.6 g, 32.1 mmol), formaldehyde (37% in water) (3.25 ml), KOH (1.4 g, 25 mmol) in water (45 ml) was stirred at 50° C. for 20 h. The reaction was acidified with 1 N HCl to give a white precipitate. The solids were collected dried under vacuum to give the 5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione (2.01 g, 44%) as a white solid.

Workup

  1. customto give a white precipitate
  2. customThe solids were collected
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3abb09e205ff4e8abed8834728a6277f
Source dataset
uspto-grants-2006_09
Patent number
US07101883B2

Reaction notes

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