Tetrabutylammonium Fluoride → HCID 66857745, compound

HRID 253030Notes

Reaction equation

HRID 253030 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:20][C:19]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][Si](C(C)(C)C)(C)C)[CH:31]=4)=[N:18][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:44])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[S:23][C:22]3[C:21]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[N:20][C:19]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=4)=[N:18][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66857607HCID 66857607, compound

Product 1

HCID 66857745HCID 66857745, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-phenyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl}-piperidin-4-yl)-carbamic acid tert-butyl ester (250 mg, 0.39 mmol) was dissolved in THF (4 mL), to this was added TBAF (1.4 eq., 0.55 mL). After 30 min. the reaction mixture was quenched with silica, evaporated in vacuo and purified by chromatography to give {1-[2-(3-hydroxy-phenyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester as a white solid (179 mg, 88%).

Workup

  1. customAfter 30 min. the reaction mixture was quenched with silica
  2. customevaporated in vacuo
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-bb454d934d874b9a895e440b32dd1913
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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