Ammonium formate → 1-(1-Acetylpiperidin-4-yl)-3-(3,4-dimethoxybenzyl)-6-hydroxyquinazoline-2,4(1H,3H)-dione

HRID 80470Notes

Reaction equation

HRID 80470 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20]CC4C=CC=CC=4)=[CH:17][CH:18]=3)[C:13](=[O:28])[N:12]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)[C:11]2=[O:40])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[C:13](=[O:28])[N:12]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=3)[C:11]2=[O:40])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59587162HCID 59587162, compound

Product 1

HCID 252528861-(1-Acetylpiperidin-4-yl)-3-(3,4-dimethoxybenzyl)-6-hydroxyquinazoline-2,4(1H,3H)-dioneYield 89.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.64 g of 1-(1-acetylpiperidin-4-yl)-6-(benzyloxy)-3-(3,4-dimethoxybenzyl)quinazoline-2,4(1H,3H)-dione obtained in stage 2.1, 0.44 g of ammonium formate and 0.125 g of Pd/C (10%) in 10 ml of EtOH purged beforehand with nitrogen is irradiated under a microwave field at 80° C. for 2 h 00. The mixture is filtered and the filtrate is evaporated under reduced pressure to give 0.48 g of the expected product.

Workup

  1. customis irradiated under a microwave field at 80° C. for 2 h 00
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-222c3c1ffe5c489689eeb030771a9218
Source dataset
uspto-grants-2014_09
Patent number
US08846654B2

Reaction notes

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