HCID 131736971, compound → Tert-butyl-4-(3-amino-4-(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-ylamino)phenyl)piperidine-1-carboxylate

HRID 58142Notes

Reaction equation

HRID 58142 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[C:25]([N:27]([CH3:51])[C:28]([N:30]([C:39]4[C:44]([Cl:45])=[C:43]([O:46][CH3:47])[CH:42]=[C:41]([O:48][CH3:49])[C:40]=4[Cl:50])[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:29])[N:24]=[CH:23][N:22]=3)=[C:16]([N+:52]([O-])=O)[CH:15]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.ClC1C=CC=CC=1.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[CH:26]=[C:25]([N:27]([CH3:51])[C:28]([N:30]([C:39]4[C:40]([Cl:50])=[C:41]([O:48][CH3:49])[CH:42]=[C:43]([O:46][CH3:47])[C:44]=4[Cl:45])[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:29])[N:24]=[CH:23][N:22]=3)=[C:16]([NH2:52])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 131736971HCID 131736971, compound

Product 1

HCID 131736970Tert-butyl-4-(3-amino-4-(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-ylamino)phenyl)piperidine-1-carboxylateYield 37%

Reagents, catalysts & solvents 3

HCID 7964ChlorobenzeneCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl-4-(4-(6-(3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)ureido)pyrimidin-4-ylamino)-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (380 g, 0.473 mmol) in MeOH (10 mL) was added PtO2 (38 mg, 10% wt) and one drop of chlorobenzene at room temperature, the resulting mixture was stirred under hydrogen atmosphere (1 atm) overnight. The reaction was filtered and concentrated. The residue was purified by flash chromatography on silica to obtain the title compound (130 mg, yield: 37%). MS (ESI): 776 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-3521bf65a1874946ae20b26fe36c97df
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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