5-Chloro-2(1H)-pyrimidinone → 5-Chloro-1-(4-methylthiophenacyl)pyrimidin-2-one

HRID 980177Notes

Reaction equation

HRID 980177 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[S:12]>C(N(CC)CC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[S:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 183681522-Bromo-4'-methylthioacetophenone

Product 1

HCID 537912715-Chloro-1-(4-methylthiophenacyl)pyrimidin-2-oneYield 63.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (312 mg) and 2-bromo-4'-methylthioacetophenone (525 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 2.25 hours. The resulting suspension was concentrated at reduced pressure then diluted with water (50 ml). The collected precipitate was crystallised from acetone to give the title pyrimidinone (404 mg,); m.p. 192°-197°, λmaxEtOH 229 nm (ε 14450), 312 nm (ε 21470), λinf 239.5 nm (ε 9930).

Workup

  1. concentrationThe resulting suspension was concentrated at reduced pressure
  2. additionthen diluted with water (50 ml)
  3. customThe collected precipitate was crystallised from acetone

Sources & evidence

ORD record
ord-bf3f0cab3246439a8dc2f70650dcfbf8
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

Loading…