Potassium Carbonate → 4-[(3-Chloro-2-fluorophenyl)amino]-7-(2-methoxyethoxy)quinazoline-6-carbaldehyde

HRID 1867732Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4]Cl.[Cl:6][C:7]1[C:8]([F:27])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:26])=[C:21]([CH:24]=[O:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:6][C:7]1[C:8]([F:27])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:4][CH2:3][O:2][CH3:1])=[C:21]([CH:24]=[O:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-Chloroethyl methyl ether (0.967 g, 6.2 mmol) was added to a stirred suspension of 4-[(3-chloro-2-fluorophenyl)amino]-7-hydroxyquinazoline-6-carbaldehyde (1.0 g, 3.1 mmol) and K2CO3 (1.30 g, 9.45 mmol) in dimethyl formamide (10 ml) at room temperature. The resulting suspension was heated at 90° C. for 8 hours, cooled to room temperature, concentrated and purified by preparative LCMS (standard basic system) to give 4-[(3-chloro-2-fluorophenyl)amino]-7-(2-methoxyethoxy)quinazoline-6-carbaldehyde as a pale yellow solid, (0.150 g, 15%); Mass Spectrum: (M+H)+ 376.

Workup

temperaturecooled to room temperature
concentrationconcentrated
custompurified by preparative LCMS (standard basic system)

Sources & evidence

ORD record: ord-637540fe938041acad0f730f1d94255b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632840B2

Reaction notes

Loading…