Homoallyl bromide → 1-(3-Butenyl)-5-bromopyrimid-2-one

HRID 1075177Notes

Reaction equation

HRID 1075177 reaction equation
[K].[Br:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Br[CH2:11][CH2:12][CH:13]=[CH2:14]>CO>[CH2:14]([N:5]1[CH:4]=[C:3]([Br:2])[CH:8]=[N:7][C:6]1=[O:9])[CH2:13][CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 21241Homoallyl bromideHCID 1014945-Bromo-2(1H)-pyrimidinoneHCID 5462222Potassium

Product 1

HCID 204942961-(3-Butenyl)-5-bromopyrimid-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the potassium salt of 5-bromopyrimid-2-one (0.01 mol) and 4-bromo-1-butene (0.015 mol) was heated in methanol (60 ml) at 70° C. for 40 h. The reaction mixture was then evaporated and the mixture extracted with chloroform. This solution was washed with 1 N NaOH (5 ml). with water (5 ml) and dried (MgSO4) before evaporating; yield 50%, m.p. 127°-128° C. (acetone). (Found: C, 42.06; H, 3.94. Calc. for C8H9BrN2O: C, 41.94; H, 3.96).

Workup

  1. customThe reaction mixture was then evaporated
  2. extractionthe mixture extracted with chloroform
  3. washThis solution was washed with 1 N NaOH (5 ml)
  4. dry with materialwith water (5 ml) and dried (MgSO4)
  5. custombefore evaporating

Sources & evidence

ORD record
ord-c827da2bd0484d6e871f7e697a2c3aef
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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