Allyl isocyanate → 1-Allylcarbamoyl-5-bromopyrimidin-2-one

HRID 1632964Notes

Reaction equation

HRID 1632964 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:9]([N:12]=[C:13]=[O:14])[CH:10]=[CH2:11]>CN(C)C=O>[CH2:9]([NH:12][C:13]([N:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[N:6][C:5]1=[O:8])=[O:14])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 15123Allyl isocyanateHCID 1014945-Bromo-2(1H)-pyrimidinone

Product 1

HCID 204416441-Allylcarbamoyl-5-bromopyrimidin-2-oneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromopyrimidin-2-one (2 mmol) and allylisocyanate (3 mmol) in dimethyl formamide (2 ml) was stirred together at room temperature until a clear solution resulted (ca. 3 h) before the solvent was distilled off at 1 mmHg, the residue triturated with ether and then with water; the residue was the title compound, yield 59%. MS (70 eV) m/e: 257/255 (M,O), 176 (31), 174 (33), 148 (9), 106 (8), 104 (8), 95 (60), 83 (20), 56 (100).

Workup

  1. customresulted (ca. 3 h) before the solvent
  2. distillationwas distilled off at 1 mmHg
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-ea08500600f44ce5b50b03bf7f0bd7e0
Source dataset
uspto-grants-1984_10
Patent number
US04478839

Reaction notes

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