Acetic Acid → HCID 178481542, compound

HRID 2258473Notes

Reaction equation

HRID 2258473 reaction equation
N[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1.Cl.C(O)(=[O:20])C>>[OH:20][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 16492566-Amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 178481542HCID 178481542, compoundYield 68%

Conditions

Temperature
100 °C

Procedure

6-Amino-3-methyl-1-phenyluracil as obtained in Reference Example 1 (8.7 g, 40 mM) was dissolved in 80 ml of acetic acid and hydrochloric acid (16 ml) was added, followed by heating at 100° C. for 1 hour. The solvent acetic acid was then distilled off under reduced pressure and water war added to the residue. The pH of the resulting solution was adjusted to 1 by adding hydrochloric acid and a product was extracted with dichloromethane. After the solvent dichloromethane was distilled off under reduced pressure from the dichloromethane layer, crystallization with ethanol was performed to give 6-hydroxy-3-methyl-1-phenyluracil (yield: 5.9 g, or 68% based on 6-amino-3-methyl-1-phenyluracil).

Workup

  1. distillationThe solvent acetic acid was then distilled off under reduced pressure and water war
  2. additionadded to the residue
  3. additionby adding hydrochloric acid
  4. extractiona product was extracted with dichloromethane
  5. distillationAfter the solvent dichloromethane was distilled off under reduced pressure from the dichloromethane layer, crystallization with ethanol

Sources & evidence

ORD record
ord-05a1dbe9acbc41669f9f1ebfef38eac1
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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