Phenyl isocyanate → HCID 58138343, compound

HRID 1465907Notes

Reaction equation

HRID 1465907 reaction equation
[F:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[N:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:19]=[O:20]>C1COCC1>[F:1][C:2]1[C:3]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:4][C:5](=[O:8])[N:6]([C:19]([NH:18][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH:7]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 178517768HCID 178517768, compound

Product 1

HCID 58138343HCID 58138343, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 25 mL screw-top vial was charged with 5-fluoro-4-(2-fluorobenzylamino)pyrimidin-2-ol (74.3 mg, 0.313 mmol), THF (2 mL), and isocyanatobenzene (0.33 mL, 0.313 mmol). The resulting mixture was then agitated on an orbital shaker for 4.5 h at which time it was concentrated to dryness in vacuo. The dried material was then purified by normal phase chromatography (gradient, EtOAc/Hexane) to provide 5-fluoro-4-(2-fluorobenzylamino)-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide (75.3 mg, 68%) as a white solid: mp 154-157° C.; 1H NMR (400 MHz, CDCl3) δ 12.65 (s, 1H), 8.51 (d, J=7.1 Hz, 1H), 7.63-7.55 (m, 2H), 7.46 (td, J=7.5, 1.7 Hz, 1H), 7.41-7.28 (m, 3H), 7.19-7.05 (m, 3H), 6.03 (s, 1H), 4.86 (d, J=5.9 Hz, 2H); ESIMS m/z 355 ([M−H]−).

Workup

  1. concentrationwas concentrated to dryness in vacuo
  2. customThe dried material was then purified by normal phase chromatography (gradient, EtOAc/Hexane)

Sources & evidence

ORD record
ord-1652e0f47993406c945be7c5cfc7bbf0
Source dataset
uspto-grants-2015_04
Patent number
US09000002B2

Reaction notes

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