5-Chloro-2(1H)-pyrimidinone → HCID 12791246, compound

HRID 1906151Notes

Reaction equation

HRID 1906151 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[O:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[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[O:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-One

Product 1

HCID 12791246HCID 12791246, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (522 mg) and 2-bromoacetylbenzo[b]furan (960 mg) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 50 min the reaction mixture was cooled to 3° C. and the solid collected. The filtrate was evaporated and the residue was subjected to preparative thin-layer chromatography developing with chloroform-ethanol (50:1) (4 runs) which gave a yellow solid. The two solids were combined and crystallised twice from acetone to give the title pyrimidinone (415 mg) m.p. 202°-205° C., λmax (EtOH) 227.5 nm (ε14,060), 298 nm (ε20,930).

Workup

  1. temperatureAfter 50 min the reaction mixture was cooled to 3° C.
  2. customthe solid collected
  3. customThe filtrate was evaporated
  4. customgave a yellow solid
  5. customcrystallised twice from acetone

Sources & evidence

ORD record
ord-4668a9f7cfd746cbb4638a8b98a93041
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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