1,3-Difluoro-5-isocyanatobenzene → HCID 90266348, compound

HRID 631841

Reaction equation

HRID 631841 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]=[C:9]=[O:10])[CH:5]=[C:4]([F:11])[CH:3]=1.[F:12][C:13]1[C:14](=[NH:21])[N:15]([CH3:20])[C:16](=[O:19])[NH:17][CH:18]=1>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([N:17]2[CH:18]=[C:13]([F:12])[C:14](=[NH:21])[N:15]([CH3:20])[C:16]2=[O:19])=[O:10])[CH:5]=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 27792821,3-Difluoro-5-isocyanatobenzeneHCID 178481639HCID 178481639, compound

Product 1

HCID 90266348HCID 90266348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Difluoro-5-isocyanatobenzene (119 mg, 0.769 mmol) was added to a solution of 5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1H)-one (100 mg, 0.699 mmol) in DMF (1.8 mL) and stirred overnight at room temperature. The solution was then concentrated under vacuum and the resulting residue stirred in dichloromethane (2 mL) for 30 min. The solids were filtered and washed with dichloromethane (2×3 mL) and dried under vacuum to afford the title compound; mp 203.0-204.5° C.; 1H NMR (400 MHz, CDCl3) δ 11.03 (s, 1H), 9.87 (s, 1H), 7.68 (d, J=6.2 Hz, 1H), 7.25 (d, J=7.4 Hz, 2H), 6.80 (s, 1H), 3.25 (s, 3H); 13C NMR (101 MHz, DMSO-d6) δ 163.77, 163.62, 161.36, 161.21, 158.57, 149.14, 146.14, 145.90, 142.72, 142.58, 142.44, 138.68, 136.41, 122.85, 122.52, 101.05, 100.76, 97.32, 97.06, 96.79, 29.43; ESIMS m/z 299.0 ([M+H]+).

Workup

  1. concentrationThe solution was then concentrated under vacuum
  2. stirringthe resulting residue stirred in dichloromethane (2 mL) for 30 min
  3. filtrationThe solids were filtered
  4. washwashed with dichloromethane (2×3 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7ec31520f4b34247abd0985fff98ba0e
Source dataset
uspto-grants-2016_04
Patent number
US09321734B2

Linked notes

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