3-(2,6-Dichloro-3,5-dimethoxyphenyl)-1-(6-(4-(4-ethylpiperazin-1-yl)-2-nitrophenylamino)pyrimidin-4-yl)-1-methylurea → 1-(6-((2-Amino-4-(4-ethylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylurea

HRID 58138Notes

Reaction equation

HRID 58138 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13][C:14](=[O:41])[N:15]([C:17]1[CH:22]=[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][N:33]([CH2:36][CH3:37])[CH2:32][CH2:31]3)=[CH:26][C:25]=2[N+:38]([O-])=O)[N:20]=[CH:19][N:18]=1)[CH3:16]>C1COCC1.CO.[Ni]>[NH2:38][C:25]1[CH:26]=[C:27]([N:30]2[CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH2:35]2)[CH:28]=[CH:29][C:24]=1[NH:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]([N:15]([CH3:16])[C:14]([NH:13][C:3]2[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=2[Cl:1])=[O:41])[CH:22]=1

Participants

5

Reactant 1

HCID 1180262793-(2,6-Dichloro-3,5-dimethoxyphenyl)-1-(6-(4-(4-ethylpiperazin-1-yl)-2-nitrophenylamino)pyrimidin-4-yl)-1-methylurea

Product 1

HCID 1180245461-(6-((2-Amino-4-(4-ethylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methylureaYield 89.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(6-(4-(4-ethylpiperazin-1-yl)-2-nitrophenylamino)pyrimidin-4-yl)-1-methylurea (330 g, 0.546 mmol) in THF (20 mL) and MeOH (20 mL) was added Raney-Ni (suspension in water) at room temperature, the resulting mixture was stirred for 3 hours under hydrogen atmosphere (1 atm). The reaction was filtered and concentrated. The residue was washed twice with MeOH to obtain the title compound (280 mg, purity: 90%), which was used directly in the next step. MS (ESI): 575 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. washThe residue was washed twice with MeOH

Sources & evidence

ORD record
ord-6864a0c1ed3041fd932c7f6aa868aef7
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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