Chlorophenyl isocyanate → HCID 58166395, compound

HRID 1405992Notes

Reaction equation

HRID 1405992 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH2:9][CH:10]2[CH2:12][CH2:11]2)[C:4](=[O:13])[N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>CC#N>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]([NH:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH2:9][CH:10]2[CH2:12][CH2:11]2)[C:4](=[O:13])[N:3]=1)=[O:23]

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 58166432HCID 58166432, compound

Product 1

HCID 58166395HCID 58166395, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-amino-1-(cyclopropylmethyl)-5-fluoropyrimidin-2(1H)-one (150 mg, 0.819 mmol) in dry CH3CN (7.5 mL) at room temperature and under nitrogen was added 2-chlorophenylisocyanate (138.3 mg, 0.90 mmol). After stirring for 1 h, the crude reaction mixture was filtered, and the solids were rinsed with CH3CN (10 mL). The collected filtrate was then concentrated in vacuo and dried under high vacuum to afford 1-(2-chlorophenyl)-3-(1-(cyclopropylmethyl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)urea (160 mg, 58%) as an off-white solid: mp 197-199° C.; 1H NMR (400 MHz, methanol-d4) δ 8.26 (d, J=6.0 Hz, 1H), 8.21 (dd, J=8.3, 1.5 Hz, 1H), 7.47 (dd, J=8.0, 1.4 Hz, 1H), 7.35-7.28 (m, 1H), 7.13 (td, J=7.8, 1.5 Hz, 1H), 3.74 (d, J=7.3 Hz, 2H), 1.32 (m, 1H), 0.69-0.58 (m, 2H), 0.50-0.38 (m, 2H); ESIMS m/z 337 ([M+H]+).

Workup

  1. customthe crude reaction mixture
  2. filtrationwas filtered
  3. washthe solids were rinsed with CH3CN (10 mL)
  4. concentrationThe collected filtrate was then concentrated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d0d559ca56cd41c1a730bc9250b442b1
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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