Water → HCID 10411292, compound

HRID 859859Notes

Reaction equation

HRID 859859 reaction equation
C([C:5]1[C:13]2[N:12]=[C:11]([CH:14]([F:16])[F:15])[N:10]([C:17]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH:24]4[CH2:28][OH:29])[CH:20]=[C:19]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[N:18]=3)[C:9]=2[C:8](C)=[C:7](C)[C:6]=1O[SiH3])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH2:58]>C1COCC1>[F:15][CH:14]([F:16])[C:11]1[N:10]([C:17]2[N:22]=[C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH2:28][OH:29])[CH:20]=[C:19]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:18]=2)[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:58])[C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 178431815HCID 178431815, compound

Product 1

HCID 10411292HCID 10411292, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

213 mg (0.38 mmol) of 2-(4-tert-butyldimethyl-silyloxy-2-difluoromethylbenzimidazol-1-yl)-4-(2-hydroxymethylpyrrolidin-1-yl)-6-morpholinopyrimidine dissolved in anhydrous THF (7 ml) was added with tetra-n-butylammoniumfluoride (0.4 ml, 1M THF solution) at room temperature and stirred for 30 minutes. The reaction solution was added with water, extracted several times with ethyl acetate, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was removed under the reduced pressure and the residue was purified by silica gel column chromatography (n-hexane ethyl acetate=1:4) to obtain 101 mg (yield: 60%) of the titled compound as colorless crystals.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washwashed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under the reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane ethyl acetate=1:4)

Sources & evidence

ORD record
ord-f2eba2a8bcb24e82bb56597c70575970
Source dataset
uspto-grants-2006_12
Patent number
US07153853B2

Reaction notes

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