Water → 6-(3-chloropropoxy)-N-(4-fluorophenyl)-7-methoxyquinazolin-4-amine

HRID 712402Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][CH2:30][CH2:31][Cl:32].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([O:19][CH2:29][CH2:30][CH2:31][Cl:32])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 4-((4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (1.83 g), K2CO3 (2.21 g), in DMF (20 mL) was added 1-bromo-3-chloropropane (1.90 mL) at rt, the mixture was stirred at 40° C. overnight. The reaction mixture was poured into water and filtered. The filter residue was purified by a silica gel column chromatography (eluting agent: 3:1 (v/v) PE/EA) to give the title compound as a white solid (2.11 g, 91.02%).

Workup

filtrationfiltered
customThe filter residue was purified by a silica gel column chromatography (eluting agent: 3:1 (v/v) PE/EA)

Sources & evidence

ORD record: ord-a5290bf0ffe442178d97b09a68f5d532
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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