Allyl bromide → 1-Allyl-5-fluoropyrimid-2-one

HRID 1075148Notes

Reaction equation

HRID 1075148 reaction equation
[Na].[F:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.[CH2:10](Br)[CH:11]=[CH2:12]>CO>[CH2:12]([N:5]1[CH:4]=[C:3]([F:2])[CH:8]=[N:7][C:6]1=[O:9])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 1014985-Fluoropyrimidin-2-oneHCID 5360545Sodium

Product 1

HCID 204942921-Allyl-5-fluoropyrimid-2-oneYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The sodium salt of 5-fluoropyrimid-2-one (0.01 mol) was dissolved in methanol (100 ml) and allyl bromide (0.015 mol) added gradually at room temperature and the reaction allowed to proceed until neutral pH had been reached. The reaction mixture was then concentrated at reduced pressure and the residue extracted with chloroform (100 ml). The chloroform solution was washed with water (2×5 ml) and dried before evaporation; Yield 48%, m.p. 88°-90° C. after recrystallisation from acetone: (Found: C, 55.10; H, 4.80. Calc. for C7H7FN2O: C, 54.56; H, 4.58.

Workup

  1. concentrationThe reaction mixture was then concentrated at reduced pressure
  2. extractionthe residue extracted with chloroform (100 ml)
  3. washThe chloroform solution was washed with water (2×5 ml)
  4. customdried before evaporation
  5. customYield 48%, m.p. 88°-90° C. after recrystallisation from acetone

Sources & evidence

ORD record
ord-7f538c8bc6dd46fe98a99364c44b9bf8
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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