Potassium tert-butoxide → HCID 118676900, compound

HRID 630552Notes

Reaction equation

HRID 630552 reaction equation
CC(C)([O-])C.[K+].[I:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[CH:14][CH:15]=2)[NH:10][CH:9]=1.Cl[C:26]1[N:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[CH:28][N:27]=1>CN(C=O)C.O>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C:29]1[CH:30]=[N:31][C:26]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[O:18])[CH:12]=3)[C:8]([I:7])=[CH:9]2)=[N:27][CH:28]=1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 463120562-Chloro-5-(2-fluorophenyl)pyrimidineHCID 118676854HCID 118676854, compound

Product 1

HCID 118676900HCID 118676900, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (236 mg, 2.106 mmol, 1.5 eq), compound 354a) (500 mg, 1.404 mmol, 1.0 eq) and 2-chloro-5-(2-fluorophenyl)pyrimidine (292 mg, 1.404 mmol, 1.0 eq) in DMF (10 mL) were stirred at 120° C. for 5 h. The reaction mixture was cooled to room temperature, diluted with water (15 mL), and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography [100-200 mesh silica; ethyl acetate/pet ether=7:3]. Yield: 400 mg (53% of theory).

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography [100-200 mesh silica; ethyl acetate/pet ether=7:3]

Sources & evidence

ORD record
ord-37f132ba89594da4ab7224b0bbb01a82
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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