Benzene, 1-chloro-3-isocyanato- → 4-amino-N-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide

HRID 1038950Notes

Reaction equation

HRID 1038950 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([N:17]=[C:18]=[O:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([Cl:10])[CH:12]=2)=[O:19])[C:4](=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 178509007HCID 178509007, compound

Product 1

HCID 581383304-amino-N-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure of Example 5 but using tetrahydrofuran (THF) instead of DMF as solvent, 4-amino-5-fluoro-pyrimidin-2-ol (0.25 g, 1.94 mmol) and 3-chlorophenyl isocyanate (0.260 mL, 2.13 mmol) were reacted to yield 4-amino-N-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (0.45 g, 82%) as a white solid: mp 250-252° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.82 (s, 1H), 8.65 (s, 1H), 8.43 (d, J=7.3 Hz, 1H), 8.35 (s, 1H), 7.29-7.20 (m, 2H), 7.06 (d, J=7.4 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H); ESIMS m/z 280.9 ([M−H]−).

Sources & evidence

ORD record
ord-4eb91d1ecf904063ab628da8293be8b1
Source dataset
uspto-grants-2013_10
Patent number
US08552020B2

Reaction notes

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