Water → HCID 9828564, compound

HRID 1433411Notes

Reaction equation

HRID 1433411 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:20][CH:19]=4)[N:15](COCC[Si](C)(C)C)[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:4][C:3]=1[NH:40][C:41]([NH:43][CH:44]1[CH2:46][CH2:45]1)=[O:42].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]3[CH:17]=[C:16]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]([CH2:28][CH3:29])[CH2:30][CH3:31])=[CH:22][CH:23]=4)[NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:5]=[CH:4][C:3]=1[NH:40][C:41]([NH:43][CH:44]1[CH2:46][CH2:45]1)=[O:42]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 58930874HCID 58930874, compound

Product 1

HCID 9828564HCID 9828564, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{2-Chloro-4-[6-[4-(2-diethylaminoethoxy)-phenyl]-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-phenyl}-3-cyclopropylurea (40 mg, 0.0601 mmol) was dissolved in 1 ml of tetrahydrofuran, and then 0.5 ml (8.3 equivalents) of tetrabutylammonium fluoride (1M tetrahydrofuran solution) was added dropwise and the mixture was refluxed for 2 hours. After returning to room temperature, 3 ml of water was added, the mixture was allowed to stand for 3 hours, and the precipitating crystals were filtered out, washed with water and ether:hexane=1:1 and dried under reduced pressure to obtain 22 mg of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customAfter returning to room temperature
  3. filtrationthe precipitating crystals were filtered out
  4. washwashed with water and ether
  5. dry with materialhexane=1:1 and dried under reduced pressure

Sources & evidence

ORD record
ord-506c07ce601c49e88b019cecdd58b993
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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