2,4-Dichloro-6,7-dimethoxyquinazoline → 2-Chloro-4,6,7-trimethoxyquinazoline

HRID 1274133Notes

Reaction equation

[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[N:14]=[C:13](Cl)[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:16][CH3:17])[CH:11]=2)[N:6]=1>CO>[Cl:4][C:5]1[N:14]=[C:13]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[C:10]([O:16][CH3:17])[CH:11]=2)[N:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Sodium methoxide (0.12 g, 2.2 mmole) was added to a solution of 2,4-dichloro-6,7-dimethoxyquinazoline (0.52 g, 2 mmol) in methanol (20 mL) at 25° C. The mixture was stirred at 25° C. for 12 h and was concentrated in vacuo to give a white solid residue. Purification of the residue by flash column chromatography (gradient elution 30 to 60% EtOAc/hexanes) provided the title compound (0.51 g, quantitative yield): TLC (Rf =0.50; CH2Cl2); 1H NMR (CDCl3) δ 7.33 (s, 1H), 7.21 (s, 1H), 4.20 (s, 3H), 4.01 (s, 6H); 13C NMR (CDCl3) δ 166.9, 156.1, 154.3, 149.8, 149.5, 109.0, 106.2, 101.4, 56.4, 56.3, 55.0; HRMS (FAB) m/z 255.0531 (M+H)+ (C11H11N2O3Cl requires 255.0536); Anal. (C11H11N2O3Cl·1/2H2O·1/4CH3OH) C, H, N.

Workup

concentrationwas concentrated in vacuo
customto give a white solid residue
customPurification of the residue
washby flash column chromatography (gradient elution 30 to 60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-bd123e150c514d6d9df1211663868abc
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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