Ammonia → 7-(benzyloxy)-5-isopropoxyquinazolin-4(3H)-one

HRID 639980Notes

Reaction equation

HRID 639980 reaction equation
C(OC[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:15][C:16]=2[O:20][CH:21]([CH3:23])[CH3:22])[N:11]=[CH:10]1)(=O)C(C)(C)C.N>CO>[CH2:25]([O:24][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[NH:9][CH:10]=[N:11]2)=[C:16]([O:20][CH:21]([CH3:23])[CH3:22])[CH:15]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68639837[7-(benzyloxy)-5-isopropoxy-4-oxoquinazolin-3(4H)-yl]methyl pivalate

Product 1

HCID 1355106847-(benzyloxy)-5-isopropoxyquinazolin-4(3H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[7-(benzyloxy)-5-isopropoxy-4-oxoquinazolin-3(4H)-yl]methyl pivalate was stirred in a 7N solution of ammonia in methanol (250 ml) at room temperature for 24 hours. The mixture was evaporated under reduced pressure and the residue purified by silica gel chromatography eluting with a 0 to 10% mixture of methanol in dichloromethane to give 7-(benzyloxy)-5-isopropoxyquinazolin-4(3H)-one (4.6 g, 87% yield over 2 steps) as a white solid:

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue purified by silica gel chromatography
  3. washeluting with a 0 to 10% mixture of methanol in dichloromethane

Sources & evidence

ORD record
ord-b298554e27ff44a18dada374b7f913bd
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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