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

HRID 386541Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH2:9]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH2:22][CH:21](CS([O-])(=O)=O)[CH2:20][CH2:19]2)=[N:16][CH:17]=1)[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH2:9]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([O:1][C:2]3[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=3)[CH2:20][CH2:19]2)=[N:16][CH:17]=1)[CH2:10][CH3:11]

Participants

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-ylmethanesulfonate (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

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

Sources & evidence

ORD record: ord-de79a93f65bf4a728e42ed6b0c0f5551
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372837B2

Reaction notes

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