Triethylamine → 2-{4-[(1-Cyclopentylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-one

HRID 2422633Notes

Reaction equation

HRID 2422633 reaction equation
Cl[C:2]1[N:31]=[CH:30][C:5]2[N:6]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)[CH2:21][CH2:20]4)=[CH:14][CH:13]=3)[N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH:25]1([N:22]2[CH2:21][CH2:20][CH:19]([O:18][C:15]3[CH:14]=[CH:13][C:12]([C:7]4[N:8]([CH3:11])[C:9](=[O:10])[C:4]5[CH:3]=[CH:2][N:31]=[CH:30][C:5]=5[N:6]=4)=[CH:17][CH:16]=3)[CH2:24][CH2:23]2)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 117048196-Chloro-2-{4-[(1-cyclopentylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 116183352-{4-[(1-Cyclopentylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-oneYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-2-{4-[(1-cyclopentylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-one (11 mg, 0.025 mmol) produced in Example 30 and triethylamine (17 μL, 0.15 mmol) were dissolved in ethyl acetate (0.5 mL), and 10% palladium-carbon (3 mg) was added thereto and stirred in a hydrogen atmosphere at room temperature for 15 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 thin-layer chromatography (chloroform/methanol=9/1) to obtain the entitled compound (7.3 mg, 71%) as a pale brown 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 thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-fad89a3908ba49f5abaa419d37f3df3e
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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