Water → 6-(4-Benzyloxyphenyl)-4-(1H-5-indolyloxy)-7H-pyrrolo[2,3-d]pyrimidine

HRID 853307Notes

Reaction equation

HRID 853307 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(NC([N:25]1[C:33]2[C:28](=[CH:29][C:30]([O:34][C:35]3[C:36]4[CH:43]=[C:42]([C:44]5[CH:49]=[CH:48][C:47]([O:50][CH2:51][C:52]6[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=6)=[CH:46][CH:45]=5)[N:41](COCC[Si](C)(C)C)[C:37]=4[N:38]=[CH:39][N:40]=3)=[CH:31][CH:32]=2)[CH:27]=[CH:26]1)=O)C>O1CCCC1>[CH2:51]([O:50][C:47]1[CH:48]=[CH:49][C:44]([C:42]2[NH:41][C:37]3[N:38]=[CH:39][N:40]=[C:35]([O:34][C:30]4[CH:29]=[C:28]5[C:33](=[CH:32][CH:31]=4)[NH:25][CH:26]=[CH:27]5)[C:36]=3[CH:43]=2)=[CH:45][CH:46]=1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 589313905-[6-(4-benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-indole-1-carboxylic ethylamide

Product 1

HCID 589309946-(4-Benzyloxyphenyl)-4-(1H-5-indolyloxy)-7H-pyrrolo[2,3-d]pyrimidineYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After dissolving 1.5 ml of tetrahydrofuran in 22 mg of 5-[6-(4-benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-indole-1-carboxylic ethylamide, a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran was added and the mixture was refluxed for 2 hours. After returning it to room temperature, water was added and the precipitated crystals were filtered out and subjected to silica gel column chromatography (hexane-ethyl acetate) to obtain 2 mg of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customto room temperature
  3. filtrationthe precipitated crystals were filtered out

Sources & evidence

ORD record
ord-ba92be0e892144028c5b01534b22af9d
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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