Sodium hydride → N-(1-methyl-1H-pyrazol-3-yl)-6-[(6-nitropyridin-3-yl)oxy]quinazoline-4-amine

HRID 1517261Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][N:14]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=3)[N:23]=[CH:22][N:21]=2)=[N:15]1>CN(C)C=O>[CH3:13][N:14]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][C:2]4[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=4)[CH:28]=3)[N:23]=[CH:22][N:21]=2)=[N:15]1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Bromo-2-nitropyridine (460 mg, 2.3 mmol) and sodium hydride (120 mg, 3.1 mmol) were added to an N,N-dimethylformamide suspension (10 ml) of 4-[(1-methyl-1H-pyrazol-3-yl)amino]quinazolin-6-ol (500 mg, 2.1 mmol), and stirred at 60° C. for 14 hours. The reaction solution was cooled to room temperature, the precipitate was collected by filtration, washed with water. The obtained precipitate was dried, then purified by silica gel column chromatography (chloroform:methanol=96:4) to obtain N-(1-methyl-1H-pyrazol-3-yl)-6-[(6-nitropyridin-3-yl)oxy]quinazoline-4-amine (580 mg, yield: 77%) as a pale yellow solid.

Workup

temperatureThe reaction solution was cooled to room temperature
filtrationthe precipitate was collected by filtration
washwashed with water
customThe obtained precipitate was dried
custompurified by silica gel column chromatography (chloroform:methanol=96:4)

Sources & evidence

ORD record: ord-db54ad2b0a6049fdb2c24daae20a88c0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232284B2

Reaction notes

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