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

HRID 712406Notes

Reaction equation

HRID 712406 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([OH:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH2:31][CH2:32][Cl:33].O>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([O:20][CH2:30][CH2:31][CH2:32][Cl:33])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 219252124-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-ol

Product 1

HCID 867294706-(3-chloropropoxy)-N-(3-ethynylphenyl)-7-methoxyquinazolin-4-amineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-ol (5.59 g), K2CO3 (7.06 g) in DMF (60 mL) was added 1-bromo-3-chloropropane (6.06 mL) at rt, the mixture was stirred at 40° C. for 6 h. 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 (5.80 g, 77.00%).

Workup

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

Sources & evidence

ORD record
ord-fbe72fb88b5043518cd4d9d80e5aac06
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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