Potassium Carbonate → 4-(4-Bromo-2-fluorophenylamino)-7-(2,3-epoxypropoxy)-6-methoxyquinazoline

HRID 1372993Notes

Reaction equation

HRID 1372993 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[O:25][CH2:24]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:4]([F:26])[CH:3]=1.OC1C=C2C(C(NC3C=CC([Br:45])=CC=3F)=NC=N2)=CC=1OC.BrCC1OC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:45][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[O:25][CH2:24]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:4]([F:26])[CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 114402734-(4-Chloro-2-fluorophenylamino)-7-(2,3-epoxypropoxy)-6-methoxyquinazolineHCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

Product 1

HCID 179746094-(4-Bromo-2-fluorophenylamino)-7-(2,3-epoxypropoxy)-6-methoxyquinazolineYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a similar procedure to the one described in Example 2 for the preparation of 4-(4-chloro-2fluorophenylamino)-7-(2,3-epoxypropoxy)-6-methoxyquinazoline, 7-hydroxy-6-methoxy-4-(2-fluoro-4-bromophenylamino)quinazoline (6 g, 16.5 mmol) was reacted with 1-bromo-2,3-epoxypropane (1.7 ml, 19.8 mmol) in DMF (50 ml) in the presence of potassium carbonate (4.55 g, 3.3 mmol) and purified as described to give 4-(4-bromo-2-fluorophenylamino)-7-(2,3-epoxypropoxy)-6-methoxyquinazoline (1.8 g, 26%).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-6816d8f0ad844431b25d825db81a66d3
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

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