Potassium Acetate → HCID 45275351, compound

HRID 1622359Notes

Reaction equation

HRID 1622359 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1.C([O-])(=O)C.[K+]>[Pd].C(O)(=O)C>[C:17]1([C:5]2[C:6]([N:8]3[CH2:9][CH2:10][CH:11]([C:14]([NH2:16])=[O:15])[CH2:12][CH2:13]3)=[N:7][CH:2]=[N:3][CH:4]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 45275350HCID 45275350, compound

Product 1

HCID 45275351HCID 45275351, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(2-chloro-5-phenylpyrimidin-4-yl)piperidine-4-carboxamide E32 (35 mg, 0.11 mmol), potassium acetate (22 mg, 0.22 mmol) and 10% wt palladium on carbon (3.5 mg) in acetic acid (2 mL) was stirred under an atmosphere of hydrogen (1 atm) for 18 h. The mixture was filtered through celite, washed with AcOH (2×10 mL) and concentrated under reduced pressure. The crude product was purified by preparative tlc on silica gel (CH2Cl2/MeOH, 10:1) to furnish the title compound as a white solid (9 mg, 29%) m/z 283 (100%, [M+H]+); m/z (ESI) C16H19N4O requires 283.1553 found [M+H]+ 283.1549.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with AcOH (2×10 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2/MeOH, 10:1)

Sources & evidence

ORD record
ord-19026c3e6f5944eba6fc11b4997b0b8b
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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