HCID 90408675, compound → HCID 90409672, compound

HRID 2177618Notes

Reaction equation

HRID 2177618 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][N:13]=[C:12]([CH3:17])[C:11]=3[N:10]=[CH:9]2)=[N:6][CH:7]=1>CC(O)=O.[Pt]>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][NH:13][CH:12]([CH3:17])[C:11]=3[N:10]=[CH:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 1

HCID 90408675HCID 90408675, compound

Product 1

HCID 90409672HCID 90409672, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-(5-fluoropyrimidin-2-yl)-4-methyl-1H-imidazo[4,5-c]pyridine (0.90 g, 3.91 mmol) in AcOH (50 ml) was passed through a 10% Pt/C catalyst cartridge on an H-Cube© hydrogenation apparatus at a pressure of 60 bar, a temperature of 60° C., and a flow rate of 1 ml/min. The reaction was concentrated, diluted with 1N NaOH, and extracted with DCM (100 mL×3). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.47 g, 51%). MS (ESI): mass calcd. for C10H1FN6, 234.10. m/z found, 235.0 [M+H]+.

Workup

  1. customa temperature of 60° C.
  2. concentrationThe reaction was concentrated
  3. additiondiluted with 1N NaOH
  4. extractionextracted with DCM (100 mL×3)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7692f2f3c14842f4a42bdd2a42a1afd3
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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