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

HRID 1022500Notes

Reaction equation

HRID 1022500 reaction equation
C([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:18](=[O:29])[N:17]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[C:16]3=[O:41])[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[O:37][CH3:38])[CH2:30][N:17]1[C:16](=[O:41])[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([N:11]3[CH2:10][CH:9]([OH:8])[CH2:12]3)[CH:14]=2)[N:19]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:18]1=[O:29]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66732267HCID 66732267, compound

Product 1

HCID 497645353-(3,4-dimethoxybenzyl)-6-(3-hydroxyazetidin-1-yl)-1-(tetrahydro-2H-pyran-4-yl)-quinazoline-2,4(1H,3H)-dioneYield 50.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.04 g of the compound obtained in Step 10.1, 0.007 g of ammonium formate and 0.008 g of Pd/C (10%) in 7.2 ml of EtOH is irradiated in a microwave field for 1 hour at 120° C. The reaction mixture is filtered and evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0, v/v) to (95/5, v/v) to give 0.017 g of the expected product.

Workup

  1. customis irradiated in a microwave field for 1 hour at 120° C
  2. filtrationThe reaction mixture is filtered
  3. customevaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a DCM/MeOH mixture from (100/0

Sources & evidence

ORD record
ord-40ba58c657384ad49d2c03e78099596c
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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