HCID 11596764, compound → HCID 11603286, compound

HRID 2422637Notes

Reaction equation

HRID 2422637 reaction equation
Cl[C:2]1[N:29]=[CH:28][C:5]2[N:6]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:14][CH:13]=3)[N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[CH:3]=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:11][N:8]1[C:9](=[O:10])[C:4]2[CH:3]=[CH:2][N:29]=[CH:28][C:5]=2[N:6]=[C:7]1[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11596764HCID 11596764, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11603286HCID 11603286, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-3-methyl-2-[4-(3-piperidin-1-ylpropoxy)phenyl]pyrido[3,4-d]pyrimidin-4(3H)-one (42.0 mg, 0.101 mmol) produced in Example 18 was dissolved in ethyl acetate (1 mL), and 10% palladium-carbon (11 mg, 0.0101 mmol) was added thereto and stirred in a hydrogen atmosphere at room temperature for 24 hours. The reaction solution was filtered through Celite, then the Celite was washed with ethyl acetate, and the mother liquid was concentrated. The residue was purified through silica gel column chromatography (chloroform/methanol=3/1) to obtain the intended compound (16.7 mg, 44%) as a colorless solid.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with ethyl acetate
  3. concentrationthe mother liquid was concentrated
  4. customThe residue was purified through silica gel column chromatography (chloroform/methanol=3/1)

Sources & evidence

ORD record
ord-f3ab593757b44107b90184e8165445a2
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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