Potassium Carbonate → 2-{4-[(1-Cyclobutylpiperidin-4-yl)oxy]phenyl}-7-(2-fluoroethyl)-3-methyl-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione

HRID 2422635Notes

Reaction equation

HRID 2422635 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[N:19]([CH3:30])[C:20](=[O:29])[C:21]5[CH:27]=[CH:26][NH:25][C:24](=[O:28])[C:22]=5[N:23]=4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:41][CH2:42][F:43])(=O)=O>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[N:19]([CH3:30])[C:20](=[O:29])[C:21]5[CH:27]=[CH:26][N:25]([CH2:41][CH2:42][F:43])[C:24](=[O:28])[C:22]=5[N:23]=4)=[CH:14][CH:13]=3)[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 672438532-{4-[(1-Cyclobutylpiperidin-4-yl)oxy]phenyl}-3-methyl-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione

Product 1

HCID 114961612-{4-[(1-Cyclobutylpiperidin-4-yl)oxy]phenyl}-7-(2-fluoroethyl)-3-methyl-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dioneYield 4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-{4-[(1-Cyclobutylpiperidin-4-yl)oxy]phenyl}-3-methyl-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (24 mg, 0.06 mmol) and potassium carbonate (33 mg, 0.24 mmol) were stirred in DMF (0.5 mL) at room temperature, then 2-fluoroethyl tosylate (40 mg, 0.18 mmol) was dropwise added thereto and stirred at room temperature for 20 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel thin-layer chromatography (chloroform/methanol=9/1) to obtain the intended compound (1.0 mg, 4%) as a pale yellow solid.

Workup

  1. washwashed with water and saturated saline water in that order
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. customThe solvent was evaporated off
  4. customthe residue was purified through silica gel thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-7fac43ebb56c4937b1ef76d9a1cb19fc
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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