HCID 131736975, compound → HCID 131736976, compound

HRID 58156Notes

Reaction equation

HRID 58156 reaction equation
[C:1]([O:5][C:6](=[O:54])[N:7]([C:23]1[CH:28]=[C:27]([N:29]([CH3:53])[C:30]([N:32]([C:41]2[C:46]([Cl:47])=[C:45]([O:48][CH3:49])[CH:44]=[C:43]([O:50][CH3:51])[C:42]=2[Cl:52])[CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:31])[N:26]=[CH:25][N:24]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][C:9]=1[N+:20]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6](=[O:54])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[CH:10][C:9]=1[NH2:20])[C:23]1[CH:28]=[C:27]([N:29]([CH3:53])[C:30]([N:32]([C:41]2[C:42]([Cl:52])=[C:43]([O:50][CH3:51])[CH:44]=[C:45]([O:48][CH3:49])[C:46]=2[Cl:47])[CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:39])[CH3:40])=[O:31])[N:26]=[CH:25][N:24]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 131736975HCID 131736975, compound

Product 1

HCID 131736976HCID 131736976, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of {6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-ureido]-pyrimidin-4-yl}-(4-morpholin-4-yl-2-nitro-phenyl)-carbamic acid tert-butyl ester (crude, prepared above) in MeOH (20 mL) was added Raney-Ni (suspension in water) at room temperature, the resulting mixture was stirred for 2 hours under hydrogen atmosphere (1 atm). The reaction was filtered and concentrated. The residue was washed twice with MeOH to obtain title product (160 mg, yield: 70%). MS (ESI): 778 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-19dfdfe66e9a45c19be4d2af9e938f14
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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