Water → HCID 86600243, compound

HRID 2111856Notes

Reaction equation

HRID 2111856 reaction equation
[Cl:1][C:2]1[N:30]=[CH:29][C:5]2[N:6]=[C:7]([CH3:28])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:13][C:12]=3[OH:27])[C:9](=[O:10])[C:4]=2[CH:3]=1.S(C1C=CC(C)=CC=1)(O[CH2:35][CH2:36][F:37])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[N:30]=[CH:29][C:5]2[N:6]=[C:7]([CH3:28])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:13][C:12]=3[O:27][CH2:35][CH2:36][F:37])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 23151276HCID 23151276, compound

Product 1

HCID 86600243HCID 86600243, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

6-chloro-3-[2-hydroxy-4-(3-piperidin-1-ylpropoxy)phenyl]-2-methylpyrido[3,4-d]-pyrimidin-4(3H)-one (10 mg), 2-fluoroethyl tosylate (7.6 mg) and potassium carbonate (16 mg) were mixed in dimethylformamide (2 mL) and stirred at 80° C. for 10 hours. Distilled water was added, the mixture extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The product was purified by silica gel thin layer chromatography (chloroform/methanol=10/1), and the title compound (8.5 mg, 77%) was obtained as a colorless solid.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe product was purified by silica gel thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-e18669628507432eb4d51ec5b9eddb1c
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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