5-Chloro-2(1H)-pyrimidinone → HCID 12795544, compound

HRID 980178Notes

Reaction equation

HRID 980178 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]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[O: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:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 12795544HCID 12795544, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-chloropyrimidin-2-one (411 mg) and 2-bromo-4'-methylsulphonyl acetophenone (835 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for one hour. The resulting suspension was concentrated at reduced pressure then diluted with water (100 ml). The collected precipitate was crystallised from acetone, then from ethanol to give the title pyrimidinone (235 mg); m.p. 257°-258°; λmaxEtOH 242 nm (ε 23650), 286 nm (ε 1950), 334 nm (ε 1680), λinf 293 nm (ε 1850).

Workup

  1. concentrationThe resulting suspension was concentrated at reduced pressure
  2. additionthen diluted with water (100 ml)
  3. customThe collected precipitate was crystallised from acetone

Sources & evidence

ORD record
ord-7a6d1f99eee74fb7a664901b55d1f4f9
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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