Methanol → HCID 178465841, compound

HRID 536062Notes

Reaction equation

HRID 536062 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][CH:7]=[N:6][C:5]2=[O:14].CO.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:24][CH3:25]>O.CC#N>[CH2:24]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][CH:7]=[N:6][C:5]2=[O:14])[CH3:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 178486912HCID 178486912, compound

Product 1

HCID 178465841HCID 178465841, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-hydroxy-7-(methyloxy)-4(1H)-quinazolinone (1 g, 5.2 mmol) in water (12 mL), MeCN (6 mL), and MeOH (1 mL) at 25° C. was treated with Cs2CO3 (1.7 g, 5.2 mmol). After the mixture was stirred for 30 minutes, iodoethane (0.42 mL, 5.2 mmol) was added and the mixture was stirred at 60° C. for 40 hours before being cooled to room temperature. The solid was collected by filtration and washed with MeOH to give 6-(ethyloxy)-7-(methyloxy)-4(1H)-quinazolinone (560 mg, 49%). MS (m/z) 221.1 (M+H+).

Workup

  1. stirringthe mixture was stirred at 60° C. for 40 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-d7d1d399a42a4e458536dd44538e48dc
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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