Phenyl isocyanate → HCID 21846256, compound

HRID 343857Notes

Reaction equation

HRID 343857 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-991856b8b98f4e1bbfc1276e42fc6c61
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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