Dimethyl Sulfoxide → 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1895725Notes

Reaction equation

HRID 1895725 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[CH:22][N:21]=2)[CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH2:26]([C:23]1[CH:22]=[N:21][C:20]([N:17]2[CH2:18][CH2:19][CH:14]([O:1][C:2]3[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=3)[CH2:15][CH2:16]2)=[N:25][CH:24]=1)[CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 546960044-Hydroxy-2(1H)-pyridinoneHCID 866262675-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonate

Product 1

HCID 670725174-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-oneYield 40.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A stirring suspension of 4-hydroxypyridin-2(1H)-one (5.23 g, 47.1 mmol, Aldrich), 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate (11.7 g, 39.2 mmol), potassium carbonate (12.5 g, 90.0 mmol, EMD) and DMSO (48 mL) was heated at 100° C. for 3 hours and then cooled to room temperature. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The organic layers were combined and concentrated in vacuo to a brown solid. The solid was purified by flash chromatography (SiO2, 100% EtOAc and then SiO2, 10% MeOH in CH2Cl2) to yield 5.00 g of desired product as an off-white solid. MS (ESI) 315 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. concentrationconcentrated in vacuo to a brown solid
  4. customThe solid was purified by flash chromatography (SiO2, 100% EtOAc

Sources & evidence

ORD record
ord-8ccd0c323b924a1e8de625cef0537587
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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