1-(2,6-Dichloro-3,5-dimethoxy-phenyl)-3-[6-(4-dimethylaminomethyl-2-nitro phenylamino)-pyrimidin-4-yl]-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-urea → 1-[6-(2-Amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-urea

HRID 58148Notes

Reaction equation

HRID 58148 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[N:13]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:14]([N:16]([C:18]1[CH:23]=[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]([CH3:34])[CH3:33])=[CH:27][C:26]=2[N+:35]([O-])=O)[N:21]=[CH:20][N:19]=1)[CH3:17])=[O:15]>CO.ClC1C=CC=CC=1.O=[Pt]=O>[NH2:35][C:26]1[CH:27]=[C:28]([CH2:31][N:32]([CH3:34])[CH3:33])[CH:29]=[CH:30][C:25]=1[NH:24][C:22]1[N:21]=[CH:20][N:19]=[C:18]([N:16]([CH3:17])[C:14]([N: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])[CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])=[O:15])[CH:23]=1

Participants

5

Reactant 1

HCID 1317369721-(2,6-Dichloro-3,5-dimethoxy-phenyl)-3-[6-(4-dimethylaminomethyl-2-nitro phenylamino)-pyrimidin-4-yl]-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-urea

Product 1

HCID 1317369731-[6-(2-Amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-urea

Reagents, catalysts & solvents 3

HCID 7964ChlorobenzeneCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(2,6-dichloro-3,5-dimethoxy-phenyl)-3-[6-(4-dimethylaminomethyl-2-nitro-phenylamino)-pyrimidin-4-yl]-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-urea (100 g, 0.15 mmol) in MeOH (10 mL) was added 4 drops of chlorobenzene and then PtO2 (30 mg, 30% wt). The solution was stirred under hydrogen atmosphere at room temperature overnight. The reaction was filtered and concentrated. The residue was taken to the next step without further purification. MS (ESI): 650 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was taken to the next step without further purification

Sources & evidence

ORD record
ord-e3aa4daf10934ef5b60e03ae04bab335
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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