Phenyl isocyanate → 4-amino-5-fluoro-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide

HRID 1465905Notes

Reaction equation

HRID 1465905 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)C=O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([C:17]([NH:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[C:4](=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 178509007HCID 178509007, compound

Product 1

HCID 581383664-amino-5-fluoro-2-oxo-N-phenylpyrimidine-1(2H)-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol* (0.25 g, 1.94 mmol) in dry N,N-dimethylformamide (DMF; 5 mL) was added phenyl isocyanate (0.231 mL, 2.13 mmol), and the mixture was stirred at room temperature for 1 h. The suspension was suction filtered, and washed with diethyl ether (Et2O; 3×10 mL). The resulting solid was air-dried overnight to yield 4-amino-5-fluoro-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide (0.32 g, 66%) as a white solid: mp 275-277° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 12.81 (s, 1H), 8.63 (s, 1H), 8.43 (d, J=7.25 Hz, 1H), 8.35 (s, 1H), 7.55 (d, J=7.58 Hz, 2H), 7.37 (t, J=7.58 Hz, 2H), 7.13 (t, J=7.25 Hz, 1H); ESIMS m/z 247.1 ([M−H]−). 4-Amino-5-fluoropyrimidin-2-ol can be purchased commercially.

Workup

  1. filtrationsuction filtered
  2. washwashed with diethyl ether (Et2O; 3×10 mL)
  3. customThe resulting solid was air-dried overnight

Sources & evidence

ORD record
ord-860268288294438b8b2356ec0277170d
Source dataset
uspto-grants-2015_04
Patent number
US09000002B2

Reaction notes

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