Potassium tert-butoxide → HCID 54670354, compound

HRID 1426982Notes

Reaction equation

HRID 1426982 reaction equation
Br[CH2:2][C:3]([CH3:31])([CH3:30])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23]([OH:29])=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7].CC([O-])(C)C.[K+]>C1COCC1>[F:28][C:26]1[CH:27]=[C:22]2[C:23](=[O:29])[N:24]([CH:25]=1)[CH2:2][C:3]([CH3:31])([CH3:30])[CH2:4][NH:5][C:6](=[O:7])[C:8]1=[C:12]3[N:13]=[C:14]([CH:15]=[CH:16][N:11]3[N:10]=[CH:9]1)[N:17]1[C@@H:18]2[CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178440536HCID 178440536, compound

Product 1

HCID 54670354HCID 54670354, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-N-(3-bromo-2,2-dimethylpropyl)-5-(2-(5-fluoro-2-hydroxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (30 mg, 0.061 mmol) in THF (5 mL) was added drop-wise potassium 2-methylpropan-2-olate (153 μL, 0.15 mmol). The reaction was heated at 50° C. for two hours. The solvent was removed under reduced pressure and the residue was purified by silica column chromatography, eluting with 10% MeOH/DCM to provide the title compound (15 mg, 60% yield). MS (apci) m/z=411.0 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica column chromatography
  3. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-19672471c26b424eb2d024d94a5fd72c
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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