5-Chloro-2(1H)-pyrimidinone → HCID 12791252, compound

HRID 1906158Notes

Reaction equation

HRID 1906158 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[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH: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[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 113109362-bromo-1-(1H-indol-3-yl)ethanone

Product 1

HCID 12791252HCID 12791252, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-chloropyrimidin-2-one (522 mg) and 3-bromoacetylindole (1.19 g) in triethylamine (0.84 ml) and ethanol (25 ml) was stirred at room temperature. After 1.5 h the mixture was heated to 55° C. After a further 1.5 h the mixture was cooled and the resulting precipitate collected and washed with cold ethanol. Recrystallisation twice from ethyl acetate and once from ethanol gave the title pyrimidinone (660 mg), m.p. 228°-229° C., λmax (EtOH) 240 nm (ε 16,370) 300.5 nm (ε 13,090).

Workup

  1. temperatureAfter 1.5 h the mixture was heated to 55° C
  2. temperatureAfter a further 1.5 h the mixture was cooled
  3. customthe resulting precipitate collected
  4. washwashed with cold ethanol
  5. customRecrystallisation twice from ethyl acetate

Sources & evidence

ORD record
ord-ab83a1a35df74ae5b92aa9bbb23a3478
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

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