3-(Trifluoromethyl)phenyl isocyanate → 1-[4-(6-Amino-pyrimidin-4-ylmethyl)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea

HRID 1993595Notes

Reaction equation

HRID 1993595 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(NC3C=CC(CC)=CC=3)=O)=[CH:11][CH:10]=2)[CH:3]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]=[C:36]=[O:37])[CH:30]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:36]([NH:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:38])([F:39])[F:27])[CH:30]=3)=[O:37])=[CH:11][CH:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 58659424HCID 58659424, compound

Product 1

HCID 586593901-[4-(6-Amino-pyrimidin-4-ylmethyl)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared as described in Example 102 but using 6-(4-aminobenzyl)-pyrimidin-4-ylamine (see Example 157), α,α,α-trifluoro-m-tolyl-isocyanate, and DMF as the solvent. The reaction mixture is stirred for 4 h. The crude product is washed with a CH2Cl2/MeOH (99/1) solution. The title compound is obtained as a white solid: ES-MS: 387.9 [M+H]+; single peak at tR=7.12 min (System 2); Rf=0.23 (CH2Cl2/MeOH, 90/10).

Workup

  1. customThe title compound is prepared
  2. washThe crude product is washed with a CH2Cl2/MeOH (99/1) solution

Sources & evidence

ORD record
ord-11565e0212054fb4a091cf34e235fcf6
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…