Phenyl isocyanate → HCID 178521964, compound

HRID 1469121Notes

Reaction equation

HRID 1469121 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[F:8][C:7]1[C:2]([NH:1][C:17]([NH:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])=[N:3][C:4]([OH:9])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 178509007HCID 178509007, compound

Product 1

HCID 178521964HCID 178521964, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a suspension of 4-amino-5-fluoropyrimidin-2-ol (0.200 g, 1.5 mmol) in anhydrous DMF (3 mL) was added phenylisocyanate (0.251 g, 2.1 mmol) and the mixture was stirred at 23° C. for 1 h and then at 60° C. for 16 h. The reaction mixture was cooled to room temperature, and the residual solid was collected by filtration. The filter cake was washed with diethyl ether (Et2O) and dried in a vacuum oven at 40° C. for 3 h to give 1-(5-fluoro-2-hydroxypyrimidin-4-yl)-3-phenylurea as a white solid (0.210 g, 55%), which was used immediately in the next step.

Workup

  1. waitat 60° C. for 16 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe residual solid was collected by filtration
  4. washThe filter cake was washed with diethyl ether (Et2O)
  5. customdried in a vacuum oven at 40° C. for 3 h

Sources & evidence

ORD record
ord-7d87d92c5a874174a69d40886fa92bf2
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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