Water → HCID 58930900, compound

HRID 853565Notes

Reaction equation

HRID 853565 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:16]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:26][CH:25]=5)[N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)=[CH:10][C:9]=2[F:46])=[O:6])[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:16]4[CH:23]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:26][CH:25]=5)[NH:21][C:17]=4[N:18]=[CH:19][N:20]=3)=[CH:10][C:9]=2[F:46])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 58930865HCID 58930865, compound

Product 1

HCID 58930900HCID 58930900, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 65 mg of N-cyclopropyl-N′-(4-(6-(4-(2-diethylaminoethoxy)-phenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-2-fluorophenyl)urea in 2 ml of tetrahydrofuran, there was added dropwise 0.5 ml of tetrabutylammonium fluoride (1M tetrahydrofuran solution) and the mixture was refluxed for 3 hours. After returning it to room temperature, water was added, the mixture was stirred, and the precipitated crystals were filtered out, washed with water and ether-hexane (1:1) and dried under reduced pressure to obtain 25 mg of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customto room temperature
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water and ether-hexane (1:1)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-ddc2a620105c4fcbbadd29460372b693
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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