Ammonium formate → HCID 59728051, compound

HRID 2043354Notes

Reaction equation

HRID 2043354 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12]([N:14]([CH2:21][CH3:22])[CH2:15][C:16]2[NH:17][CH:18]=[N:19][CH:20]=2)[CH:11]=[C:10](Cl)[N:9]=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:13]=[C:12]([N:14]([CH2:21][CH3:22])[CH2:15][C:16]2[NH:17][CH:18]=[N:19][CH:20]=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59728215HCID 59728215, compound

Product 1

HCID 59728051HCID 59728051, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2-Benzyl-6-chloro-pyrimidin-4-yl)-ethyl-(3H-imidazol-4-ylmethyl)-amine (0.164 g, 0.5 mmol) was dissolved in methanol (3 ml), ammonium formate (0.315 g, 0.5 mmol) and palladium on charcoal (0.164 g, 10% Pd) was added and the mixture was refluxed for one hour. After cooling the catalyst was filtered off and the solvent was evaporated. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=95:5) to yield a white solid, (0.03 g, 21%); MS (ISP): 294.4 ((M+H)+.).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. temperatureAfter cooling the catalyst
  3. filtrationwas filtered off
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/methanol=95:5)
  6. customto yield a white solid, (0.03 g, 21%)

Sources & evidence

ORD record
ord-0549dea9b7284815ab831e19f43fe094
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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