Tetrabutylammonium Fluoride → HCID 66743388, compound
Reaction equation
[Si]([O:8][CH:9]1[CH2:29][CH2:28][C:12]2([NH:17][C:16]3[CH:18]=[C:19]([C:21]4[CH:22]=[N:23][NH:24][C:25]=4[CH3:26])[S:20][C:15]=3[C:14](=[O:27])[NH:13]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH:9]1[CH2:29][CH2:28][C:12]2([NH:17][C:16]3[CH:18]=[C:19]([C:21]4[CH:22]=[N:23][NH:24][C:25]=4[CH3:26])[S:20][C:15]=3[C:14](=[O:27])[NH:13]2)[CH2:11][CH2:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-6′-(5-methyl-1H-pyrazol-4-yl)-1′H-spiro[cyclohexane-1,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one (<0.450 mmol) in THF (4 mL) was added N,N,N,N-tetrabutylammonium fluoride (1.0 M in THF, 1.08 mL, 1.08 mmol). The mixture was stirred at room temperature for 16 h and at 50° C. for 1 h. The mixture was partitioned between EtOAc (20 mL) and aqueous NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (5 mL×2). The combined organic layers were washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 85:15 EtOAc/MeOH) followed by trituration with EtOAc (5 mL) to give the title compound (32.1 mg, 22%) as a pale yellow solid:
Workup
- customThe mixture was partitioned between EtOAc (20 mL) and aqueous NaHCO3 (10 mL)
- extractionThe aqueous layer was extracted with EtOAc (5 mL×2)
- washThe combined organic layers were washed with brine (5 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (Purif, silica gel, EtOAc to 85:15 EtOAc/MeOH)
Sources & evidence
- ORD record
- ord-196404aa33fe49f7a926ad14250b9c18
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691828B2
Reaction notes
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