2-Methoxyethanol → 5,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one

HRID 749192Notes

Reaction equation

HRID 749192 reaction equation
F[C:2]1[CH:11]=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][CH:6]=[N:7]2.CC(C)([O-])C.[K+].[CH3:20][O:21][CH2:22][CH2:23][OH:24].[CH3:25][O:26][CH2:27][CH2:28][O:29]CCOC>>[NH3:5].[CH3:20][O:21][CH2:22][CH2:23][O:24][C:2]1[CH:11]=[C:10]([O:29][CH2:28][CH2:27][O:26][CH3:25])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 8150DiglymeHCID 23665647Potassium tert-butoxideHCID 1355106875,7-Difluoro-3,4-dihydroquinazolin-4-one

Product 2

HCID 222AmmoniaHCID 1363519535,7-bis(2-methoxyethoxy)quinazolin-4(3H)-oneYield 99%

Procedure

5,7-difluoroquinazolin-4(3H)one (728 mg, 4 mmol) in diglyme (15 ml) and potassium tert-butoxide (4.48 g, 32 mmol) were reacted with 2-methoxyethanol (2.52 ml, 32 mmol) at 110° C. for 1 hour. The mixture was cooled and purified by chromatography on silica gel. Elution with dichloromethane:methanol (96:4) then increased polarity to dichloromethane:methanolic ammonia (95:5) yielded 5,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one (982 mg, 99% yield):

Workup

  1. temperatureThe mixture was cooled
  2. custompurified by chromatography on silica gel
  3. washElution with dichloromethane:methanol (96:4)
  4. temperaturethen increased polarity to dichloromethane

Sources & evidence

ORD record
ord-f9689fa1239d4bc69a517f720e3ce9d1
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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