Potassium Carbonate → 7-((2-Chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy4-phenoxyquinazoline

HRID 1384618Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:19][CH3:20].Cl.[Cl:22][C:23]1[CH:28]=[C:27]([CH2:29]Cl)[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:22][C:23]1[CH:28]=[C:27]([CH2:29][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:19][CH3:20])[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-hydroxy-6-methoxy-4-phenoxyquinazoline (1.1 g, 4.1 mmol), (prepared as described for the starting material in Example 13), 2-chloro-4-chloromethyl-6-methoxypyridine hydrochloride (0.88 g, 3.9 mmol) and potassium carbonate (2.0 g, 14 mmol) in DMF (20 ml) was heated at 80° C. for 1 hour. The mixture was allowed to cool, diluted with water and the precipitated product collected by filtration, washed with water and dried to give 7-((2chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy-4-phenoxyquinazoline (1.38 g, 79%). 1H NMR Spectrum: (CDCl3) 3.95(s, 3H); 4.04(s, 3H); 5.20(s, 2H); 6.70(s, 1H); 6.95(s, 1H) 7.18(m, 3H); 7.30(t, 1H); 7.40(t, 2H); 7.58(s, 1H); 8.52(s, 1H) MS-ESI: 424 [MH]+

Workup

custom(prepared
temperatureto cool
filtrationthe precipitated product collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-fb4ba10cdf7b44b1b55b00473576cabe
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258951B1

Reaction notes

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