2-[(Dimethylamino)methylidene]cyclohexane-1,3-dione → 2-(2-(tert-butyldiphenylsilyloxy)ethyl)-7,8-dihydroquinazolin-5(6H)-one

HRID 1444726Notes

Reaction equation

HRID 1444726 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]([NH2:23])=[NH:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([CH:27]=[C:28]1[C:33](=[O:34])[CH2:32][CH2:31][CH2:30][C:29]1=O)C>CCO>[Si:1]([O:18][CH2:19][CH2:20][C:21]1[N:23]=[CH:27][C:28]2[C:33](=[O:34])[CH2:32][CH2:31][CH2:30][C:29]=2[N:22]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dioneHCID 588414073-(Tert-butyldiphenylsilyloxy)propanamidine

Product 1

HCID 588413472-(2-(tert-butyldiphenylsilyloxy)ethyl)-7,8-dihydroquinazolin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(tert-butyldiphenylsilyloxy)-propanamidine (25 g, 77 mmol) and 2-((dimethylamino)methylene)cyclohexane-1,3-dione (12.8 g, 77 mmol) in 400 mL of dry EtOH was heated at 80° C. for 3 h. After cooling to room temperature, the solvent was evaporated. Flash chomatography (SiO2, EtOAc/hexane=1:1) gave the desired product as a white solid.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c5c4e49b13cf47a3bea41771f00293a5
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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