Potassium tert-butoxide → HCID 86696724, compound

HRID 2365868Notes

Reaction equation

HRID 2365868 reaction equation
CC([O-])(C)C.[K+].CS(O[CH:12]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([F:31])[CH:25]=1)[CH2:13][CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:15])(=O)=O.[O:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:39]2[N:44]=[C:43]([C:45]3[CH:50]=[CH:49][NH:48][C:47](=[O:51])[CH:46]=3)[CH:42]=[CH:41][N:40]=2)[CH2:34][CH2:33]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Si:17]([O:16][CH:14]([CH3:15])[CH2:13][CH:12]([N:48]1[CH:49]=[CH:50][C:45]([C:43]2[CH:42]=[CH:41][N:40]=[C:39]([NH:38][CH:35]3[CH2:34][CH2:33][O:32][CH2:37][CH2:36]3)[N:44]=2)=[CH:46][C:47]1=[O:51])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([F:31])[CH:25]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 86696649HCID 86696649, compoundHCID 86696725HCID 86696725, compound

Product 1

HCID 86696724HCID 86696724, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
95 °C

Procedure

Potassium 2-methylpropan-2-olate (135 mg, 1.20 mmol), tetrabutylammonium iodide (67 mg, 0.18 mmol), and a solution of 3-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)butyl methanesulfonate (0.75 mmol) in anhydrous THF (15 mL) were added to a suspension of 4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (163 mg, 0.600 mmol) in anhydrous THF (5.0 mL). The resulting mixture was stirred at 95° C. under microwave irradiation for 2 hours. The reaction was quenched with water (20 mL). The mixture was further diluted with DCM. After removal of the insoluble by filtration, the filtrate was extracted with DCM. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by Combiflash (0.5% NH3HCO3/CH3CN) to afford 1-(3-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)butyl)-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (80 mg, 26% yield). LCMS (ESI) m/z: 587.2 [M+H]+.

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. additionThe mixture was further diluted with DCM
  3. customAfter removal of the
  4. filtrationinsoluble by filtration
  5. extractionthe filtrate was extracted with DCM
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by Combiflash (0.5% NH3HCO3/CH3CN)

Sources & evidence

ORD record
ord-55fb0704c5c24d7288ef4e8b26fd726f
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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