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6-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dione → 3-(3,4-dimethoxybenzyl)-6-(1-hydroxy-1-methylethyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022496
Notes
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Reaction equation

HRID 1022496 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:9](=[O:20])[N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=1)[C:7]2=[O:32])(=[O:3])[CH3:2].[CH3:33][Mg]I>CCOCC>[CH3:31][O:30][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH3:29])[CH2:21][N:8]1[C:7](=[O:32])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:1]([OH:3])([CH3:33])[CH3:2])[CH:5]=2)[N:10]([CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:9]1=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 497644036-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dioneHCID 178418373HCID 178418373, compound

Product 1

HCID 497642843-(3,4-dimethoxybenzyl)-6-(1-hydroxy-1-methylethyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dioneYield 9.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

0.1 g of 6-acetyl-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione is added to a solution of 0.143 g of methylmagnesium iodide in 1 ml of Et2O. This mixture is stirred for 30 minutes at 0° C. and then overnight at room temperature. The reaction mixture is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with EtOAc to give 0.01 g of the expected product.

Workup

  1. customovernight
  2. customat room temperature
  3. customThe reaction mixture is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-03cf341822f3414ca147a2e0ea47c0dd
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722659B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes