Phenyl isocyanate → HCID 21846256, compound

HRID 619301Notes

Reaction equation

HRID 619301 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([F:18])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1C=CC=CC=1>[F:18][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([C:6]2[CH:5]=[C:4]([CH:19]([CH3:21])[CH3:20])[N:3]=[C:2]([NH:1][C:29]([NH:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:30])[N:7]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 1969684-(4-Fluoro-1-naphthalenyl)-6-(1-methylethyl)-2-pyrimidinamine

Product 1

HCID 21846256HCID 21846256, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine (288.3 mg) was dissolved in benzene (50 mL) and phenyl isocyanate (119.1 mg) was added. The reaction mixture was heated to reflux for 48 hours, and the solvent was removed under vacuum. The residue was chromatographed on silica gel, eluting with hexane/ethyl acetate, to yield 1-[4-(4-fluoronaphth-1-yl)-6-isopropyl-pyrimidin-2-yl]-3-phenylurea (49.1 mg), m.p. 117-178° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 hours
  3. customthe solvent was removed under vacuum
  4. customThe residue was chromatographed on silica gel
  5. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-0142468878844fe18a4187f98218ebe5
Source dataset
uspto-grants-1999_09
Patent number
US05958934

Reaction notes

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