Water → N-(3-ethynylphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-amine

HRID 403665

Reaction equation

HRID 403665 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].CS(O[CH2:28][CH2:29][O:30][CH3:31])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].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][CH2:28][CH2:29][O:30][CH3:31])[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 10796Cesium carbonateHCID 1462932-Methoxyethyl methanesulfonateHCID 219252124-(3-Ethynylphenylamino)-7-methoxyquinazolin-6-ol

Product 1

HCID 86664384N-(3-ethynylphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-amineYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-ol (2.9 g, 0.01 mol), 2-methoxyethyl methane sulfonate (4.6 g, 0.03 mol, 3 equiv), and cesium carbonate (9.9 g, 0.03 mol, 3 equiv) in DMF (100 ml) was heated to 60° C. for 12 hours. The reaction mixture was cooled to room temperature and poured into cold water, the solid was filtrated and dried to give 1.5 g product. MS (ESI) m/z: 350 (M+1).

Workup

  1. filtrationthe solid was filtrated
  2. customdried

Sources & evidence

ORD record
ord-9e6a86edf15d43158a5bd6e3022104ce
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Linked notes

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