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

HRID 2422632Notes

Reaction equation

HRID 2422632 reaction equation
Cl[C:2]1[N:30]=[CH:29][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[CH2:28][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:16]=[CH:17][C:12]([C:7]4[N:8]([CH3:11])[C:9](=[O:10])[C:4]5[CH:3]=[CH:2][N:30]=[CH:29][C:5]=5[N:6]=4)=[CH:13][CH:14]=3)[CH2:24][CH2:23]2)[CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 116690506-Chloro-2-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 117108622-{4-[(1-Cyclobutylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-oneYield 15%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-2-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-3-methylpyrido[3,4-d]pyrimidin-4(3H)-one (40.8 mg, 0.096 mmol) produced in Example 30 and triethylamine (77 μL, 0.48 mmol) were dissolved in ethyl acetate (0.5 mL), and 10% palladium-carbon (10 mg) was added thereto and stirred in a hydrogen atmosphere at room temperature for 1 hour. 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 (5.6 mg, 15%) as a pale yellow solid. The resulting compound was recrystallized from ethanol-water to give a colorless solid (m.p. 147.0-148.0° C.).

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-616c260062a1420f9a045760d075525e
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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