Water → 3-Methyl-2-({4-[(1-methyl-pyrazol-3-yl)amino]-quinazolin-6-yl}oxy)benzonitrile

HRID 2246353Notes

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:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C(O[K])(C)(C)C.O>CN(C)C(=O)C>[CH3:28][C:27]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]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23]

Participants

Conditions

Temperature: 110 °C

Procedure

4-[(1-Methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (90 mg; 0.373 mmol) and 100 mg (0.741 mmol) of 2-fluoro-3-methylbenzonitrile were added to a solution of 105 mg (0.937 mmol) of tert-butoxy potassium in 5 ml of N,N-dimethylacetamide and the mixture was stirred at 110° C. for 4 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 31 mg (yield: 23%) of the title compound as a colorless solid.

Workup

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

Sources & evidence

ORD record: ord-6526d9255daa46e3a31c4cf514226912
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687502B2

Reaction notes

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