Water → 5-Chloro-1-(2-oxo-2-phenylethyl)-2(1H)-pyrimidinone

HRID 980189Notes

Reaction equation

HRID 980189 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:17])[N:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2O)[CH:7]=1.[OH2:18]>N1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:17])[N:6]([CH2:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 20222325HCID 20222325, compound

Product 1

HCID 127955325-Chloro-1-(2-oxo-2-phenylethyl)-2(1H)-pyrimidinone

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent2×

Procedure

A solution of 5-chloro-1-(2-hydroxyphenethyl)pyrimidin-2-one (251 mg) in pyridine (6 ml) was added to the stirred suspension obtained by adding chromium trioxide (408 mg) to pyridine (4 ml). After 21/2 hours the mixture was diluted with water (10 ml) and the products were extracted with ethyl acetate (150 ml). The extract was washed with N-hydrochloric acid (2×25 ml) and water (50 ml), dried (MgSO4) and evaporated to a solid (271 mg). Crystallisation of this from ethanol followed by purification of the mother liquor material by preparative-layer chromatography gave the title pyrimidinone (48 mg), whose p.m.r. spectrum (in deuteriodimethylsulphoxide) and t.l.c. characteristics were identical to those of authentic material (vide supra).

Workup

  1. customobtained
  2. extractionthe products were extracted with ethyl acetate (150 ml)
  3. washThe extract was washed with N-hydrochloric acid (2×25 ml) and water (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a solid (271 mg)
  6. customCrystallisation of this from ethanol
  7. customfollowed by purification of the mother liquor material by preparative-layer chromatography

Sources & evidence

ORD record
ord-84afefc56f0244d2a5927d2dc6be50de
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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