Propargyl bromide → 1-Propargyl-5-chloropyrimidin-2-one

HRID 1075151Notes

Reaction equation

HRID 1075151 reaction equation
[K].[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.[CH2:10](Br)[C:11]#[CH:12]>CN(C)C=O>[CH2:12]([N:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]1=[O:9])[C:11]#[CH:10]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 5462222Potassium

Product 1

HCID 1249871-Propargyl-5-chloropyrimidin-2-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the potassium salt of 5-chloropyrimid-2-one (0.009 mol) and propargyl bromide (0.013 mol) in dimethylformamide (40 ml) was stirred at room temperature for 18 h. The solvent was then removed at reduced pressure (1 mm Hg) and the residue was extracted with chloroform (150 ml). The chloroform solution was passed through a column of Al2O3 (Woelm; 30 g, activity III). Evaporation of the chloroform eluates left a solid which was triturated with a little ether before recrystallization from EtOAc; yield 56%, m.p. 130° C. (Found: C, 50.11; H, 2.95. Calc. for C7H5ClN2O: C, 49.87; H, 2.99).

Workup

  1. customThe solvent was then removed at reduced pressure (1 mm Hg)
  2. extractionthe residue was extracted with chloroform (150 ml)
  3. customEvaporation of the chloroform
  4. waiteluates left a solid which
  5. customwas triturated with a little ether before recrystallization from EtOAc

Sources & evidence

ORD record
ord-7601d1110a25463ea8c6b9c9a7f7234f
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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