Water → 5-[6-(4-benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-indole-1-carboxylic ethylamide

HRID 387789Notes

Reaction equation

HRID 387789 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:33]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:18]3[N:19]=[CH:20][N:21]=[C:22]([O:23][C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[NH:29][CH:28]=[CH:27]5)[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:44]([NH:46][C:47](=O)[O:48]C1C=CC=CC=1)[CH3:45].O>CN(C)C=O>[CH2:44]([NH:46][C:47]([N:29]1[C:30]2[C:26](=[CH:25][C:24]([O:23][C:22]3[C:17]4[CH:16]=[C:15]([C:12]5[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]6[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=6)=[CH:14][CH:13]=5)[N:33]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:18]=4[N:19]=[CH:20][N:21]=3)=[CH:32][CH:31]=2)[CH:27]=[CH:28]1)=[O:48])[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2802346phenyl N-ethylcarbamateHCID 589308046-(4-Benzyloxyphenyl)-4-(1H-5-indolyloxy)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 589313905-[6-(4-benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-indole-1-carboxylic ethylamideYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 6-(4-benzyloxyphenyl)-4-(1H-5-indolyloxy)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine (81 mg) in 1 ml of dimethylformamide, 7 mg of sodium hydride (60% dispersion) was added, the mixture was stirred at room temperature for 5 minutes, and then 31 mg of phenyl ethylcarbamate was added and the mixture was stirred for another 2 hours. Water was then added, and ethyl acetate was used for liquid separation and extraction. The organic layer was concentrated and subjected to silica gel column chromatography (hexane-ethyl acetate) to obtain 62 mg of the title compound.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for another 2 hours
  3. customethyl acetate was used for liquid separation and extraction
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-49f9680eef2b44ae8911fa4964dac929
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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