Methyl Isocyanate → 1-N-Methylcarbamoyl-5-fluoropyrimidin-2-one

HRID 1632962Notes

Reaction equation

HRID 1632962 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[F:5][C:6]1[CH:7]=[N:8][C:9](=[O:12])[NH:10][CH:11]=1>CS(C)=O>[CH3:1][NH:2][C:3]([N:10]1[CH:11]=[C:6]([F:5])[CH:7]=[N:8][C:9]1=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 1014985-Fluoropyrimidin-2-one

Product 1

HCID 204416501-N-Methylcarbamoyl-5-fluoropyrimidin-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methylisocyanate (3.8 mmol) was added dropwise with vigorous stirring to a solution of 5-fluoropyrimidin-2-one (described in Undheim K. and Gacek M. Acta. Chem. Scand 23 (1969) 294) (2.5 mmol) in anhydrous DMSO (3.2 ml). The exothermic reaction started at once and a white solid was precipitated. The precipitate was collected after 50 minutes, washed with a little water, sucked dry, washed with ethyl acetate and dried; yield 60%, m.p. 166° C., 1H NMR (CDCl3): δ3.03 (N-Me), 8.66 (H-4), 8.71 (H-6).

Workup

  1. customThe exothermic reaction
  2. customwas precipitated
  3. customThe precipitate was collected after 50 minutes
  4. washwashed with a little water
  5. customsucked dry
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-921b1f13a433450699c7b6a4c21790a2
Source dataset
uspto-grants-1984_10
Patent number
US04478839

Reaction notes

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