5-Chloro-2(1H)-pyrimidinone → HCID 12791248, compound

HRID 1906153Notes

Reaction equation

HRID 1906153 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:17]=[CH:16][S: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](=[O:12])[C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-one

Product 1

HCID 12791248HCID 12791248, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (522 mg) and 3-bromoacetylthiophene (1.025 g) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 1 h. the mixture was cooled to 3° C., the resulting precipitate was collected, then dried and recrystallised twice from ethanol to give the title pyrimidinone (460 mg), m.p. 227°-230° C., λmax (EtOH) 250 nm (ε 15,770), 333 nm (ε 2,690).

Workup

  1. temperatureAfter 1 h. the mixture was cooled to 3° C.
  2. customthe resulting precipitate was collected
  3. customdried
  4. customrecrystallised twice from ethanol

Sources & evidence

ORD record
ord-7658ddd44cc44a50b871eea49243254f
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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