Water → HCID 23160302, compound

HRID 2246351Notes

Reaction equation

HRID 2246351 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[N:11]=[CH:10][N:9]=2)=[N:3]1.F[C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C:27](=[O:29])[CH3:28].C(O[K])(C)(C)C.O>CN(C)C(=O)C>[CH3:26][C:25]1[C:20]([O:18][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[N:11]=[CH:10][N:9]=[C:8]3[NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)=[C:21]([C:27](=[O:29])[CH3:28])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 231602801-(2-Fluoro-3-methylphenyl)ethanoneHCID 231603824-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-olHCID 178418922HCID 178418922, compound

Product 1

HCID 23160302HCID 23160302, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (71 mg; 0.295 mmol) and 90 mg (0.592 mmol) of 1-(2-fluoro-3-methylphenyl)ethanone were added to a solution of 82 mg (0.732 mmol) of tert-butoxy potassium in 5 ml of N,N-dimethylacetamide and the mixture was stirred at 130° C. for 5 hours. Water was added to the reaction solution and the mixture was extracted with chloroform. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel chromatography (chloroform:methanol=12:1) to give 6 mg (yield: 5%) of the title compound as a colorless solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a silica gel chromatography (chloroform:methanol=12:1)

Sources & evidence

ORD record
ord-e850e3b7099f4f038dcf4354c08303f2
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

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