Dichloromethane → 3-(3,4-dimethoxybenzyl)-7-fluoro-6-hydroxy-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022487Notes

Reaction equation

HRID 1022487 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[N:15]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:14](=[O:26])[N:13]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[C:12]2=[O:38])C1C=CC=CC=1.C([O-])=O.[NH4+].C(Cl)Cl>CCO.[Pd]>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[O:34][CH3:35])[CH2:27][N:13]1[C:12](=[O:38])[C:11]2[C:16](=[CH:17][C:18]([F:19])=[C:9]([OH:8])[CH:10]=2)[N:15]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:14]1=[O:26]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 2723923Ammonium formateHCID 667325316-(benzyloxy)-3-(3,4-dimethoxybenzyl)-7-fluoro-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 497649193-(3,4-dimethoxybenzyl)-7-fluoro-6-hydroxy-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dioneYield 66.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.2 g of the compound obtained in Step 4.6, 0.036 g of ammonium formate and 0.041 g of Pd/C (10%) in 4 ml of EtOH is irradiated in a microwave field for 5 minutes at 60° C. DCM is added, the mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a PE/EtOAc mixture from (95/5, v/v) to (0/100, v/v) to give 0.11 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 5 minutes at 60° C
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a PE/EtOAc mixture from (95/5

Sources & evidence

ORD record
ord-7c03f8896d40420f9b0587273c793bac
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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