Ammonium formate → HCID 59312310, compound

HRID 2077039Notes

Reaction equation

HRID 2077039 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13][C:12]=2[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:1]([C:8]1[N:9]=[C:10]([O:26][CH3:27])[C:11]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][C:12]=2[N:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59312304HCID 59312304, compound

Product 1

HCID 59312310HCID 59312310, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,7-Dibenzyl-4-methoxy-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine of Preparation 38, Step C, (75 mg, 0.2 mmol) was dissolved in 10 ml of methanol and ammonium formate (66 mg, 1.04 mmol) and 10% palladium on carbon (20 mg) was added. The reaction was refluxed under nitrogen for 2 h. The reaction mixture was filtered through Arbocel and concentrated in vacuo. The residue was purified by column chromatography on Biotage 40S cartridge, eluting with DCM:MeOH:0.880NH3 (95:5:0.5 to 90:10:1), to afford the title compound as a colourless oil in 100% yield, 56 mg.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 2 h
  2. filtrationThe reaction mixture was filtered through Arbocel
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on Biotage 40S cartridge
  5. washeluting with DCM

Sources & evidence

ORD record
ord-db7fd64af13c49be9c05c3848b356e44
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

Loading…