Ammonium formate → 6-amino-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022492Notes

Reaction equation

HRID 1022492 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]([N+:18]([O-])=O)[CH:14]=2)[N:9]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:8]1=[O:27].C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[C:8](=[O:27])[N:7]([CH2:6][C:5]1[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:16]2=[O:17]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 49763060HCID 49763060, compound

Product 1

HCID 497630596-amino-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1 g of the compound obtained in Step 6.3, 0.36 g of ammonium formate and 0.24 g of Pd/C (10%) in 10 ml of EtOH purged beforehand with nitrogen is irradiated in a microwave field for 10 minutes at 80° C. The resulting mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with an EtOAc/DCM mixture from (0/100, v/v) to (100/0, v/v) to give the expected product.

Workup

  1. customis irradiated in a microwave field for 10 minutes at 80° C
  2. filtrationThe resulting mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with an EtOAc/DCM mixture from (0/100, v/v) to (100/0

Sources & evidence

ORD record
ord-9352292e266342e3bcbfda573a5f5baa
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

Loading…