Ethyl Bromide → 6-ethoxy-7-methoxyquinazolin-4(3H)-one

HRID 871252Notes

Reaction equation

HRID 871252 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH3:23]>O.CC#N.CO>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=[O:14])[CH3:23]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 1354464136-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354437126-ethoxy-7-methoxyquinazolin-4(3H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 21864137Acetonitrile methanol waterSolvent

Procedure

A mixture of 6-hydroxy-7-methoxyquinazoline-4(3H)-one (1.0 g, 5.2 mmol) and Cs2CO3 (1.69 g, 5.2 mmol) in H2O:MeCN:MeOH (10:5:1, 20 mL) was stirred at room temperature for 30 minutes and to it was added bromoethane (0.567 g, 5.2 mmol). Then, it was stirred at 60° C. two days. It was filtered to afford 6-ethoxy-7-methoxyquinazolin-4(3H)-one as a solid (0.550 g, 48%). 1H NMR (300 MHz, DMSO-d6) δ 8.0 (s, 1H), 7.91 (s, 1H), 7.4 (d, 1H), 7.1 (d, 1H), 4.15 (t, 2H), 3.9 (s, 3H), 1.4 (t, 3H).

Workup

  1. stirringThen, it was stirred at 60° C. two days
  2. filtrationIt was filtered

Sources & evidence

ORD record
ord-7022351b60e24c589995122ca93ee6d2
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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