Cesium carbonate → HCID 25253041, compound

HRID 403553Notes

Reaction equation

HRID 403553 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][N:22]([CH:25]=[O:26])[CH2:21][CH2:20]2)[C:8]1=[O:27].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:40][C:41]#[N:42]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:40][C:41]#[N:42])[CH:14]=2)[N:9]([CH:19]2[CH2:24][CH2:23][N:22]([CH:25]=[O:26])[CH2:21][CH2:20]2)[C:8]1=[O:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 25253040HCID 25253040, compound

Product 1

HCID 25253041HCID 25253041, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.17 g of 4-[3-(3,4-dimethoxybenzyl)-6-hydroxy-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl]piperidine-1-carbaldehyde obtained in stage 1.8 and 0.25 g of Cs2CO3 in 3 ml of DMF are stirred for 15 min at AT. 0.056 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 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 0.112 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. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-bbcdaeb78c084a65a48a0a63effec3fa
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Reaction notes

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