Ammonium formate → HCID 25070581, compound

HRID 2077038Notes

Reaction equation

HRID 2077038 reaction equation
C([N:8]1[CH2:14][CH2:13][C:12]2[C:15](Cl)=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:17]2[N:16]=[CH:15][C:12]3[CH2:13][CH2:14][NH:8][CH2:9][CH2:10][C:11]=3[N:18]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59312305HCID 59312305, compound

Product 1

HCID 25070581HCID 25070581, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Under nitrogen, a mixture of 7-benzyl-4-chloro-2-(4-methylbenzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine of Preparation 35, Step B, (150 mg, 0.40 mmol), ammonium formate (250 mg, 4.0 mmol) and 20% palladium on charcoal (15 mg) in ethanol (5 ml) was heated at 75° C. for 1 h. After returning to room temperature, the mixture was filtered through a pad of Arbocel, washing the pad with ethanol. The combined eluates were concentrated in vacuo and the residue purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.880NH3, 95:5:0.5 then 90:10:1, to afford the title compound as an oil in 85% yield, 85 mg.

Workup

  1. customAfter returning to room temperature
  2. filtrationthe mixture was filtered through a pad of Arbocel
  3. washwashing the pad with ethanol
  4. concentrationThe combined eluates were concentrated in vacuo
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-af0c7f8b432e46fba43deac7385c3928
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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