Cesium carbonate → HCID 46927308, compound

HRID 80471Notes

Reaction equation

HRID 80471 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]([OH:20])=[CH:17][CH:18]=3)[C:13](=[O:21])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)[C:11]2=[O:33])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:41][C:42]#[N:43]>CN(C=O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:41][C:42]#[N:43])=[CH:17][CH:18]=3)[C:13](=[O:21])[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=3)[C:11]2=[O:33])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 252528861-(1-Acetylpiperidin-4-yl)-3-(3,4-dimethoxybenzyl)-6-hydroxyquinazoline-2,4(1H,3H)-dione

Product 1

HCID 46927308HCID 46927308, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.12 g of 1-(1-acetylpiperidin-4-yl)-3-(3,4-dimethoxybenzyl)-6-hydroxyquinazoline-2,4(1H,3H)-dione obtained in stage 2.2 and 0.172 g of Cs2CO3 in 3 ml of DMF are stirred for 15 min at AT. 0.038 g of bromoacetonitrile is added and the reaction mixture is subsequently irradiated under a microwave field at 100° C. for 15 min. It is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an MeOH/DCM mixture, (1/99, v/v) as far as (4/96, v/v), to give 0.094 g of the expected product.

Workup

  1. customthe reaction mixture is subsequently irradiated under a microwave field at 100° C. for 15 min
  2. filtrationIt is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-5e7b2ea33f0849a1aa9cbe7274ee3703
Source dataset
uspto-grants-2014_09
Patent number
US08846654B2

Reaction notes

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