Cesium carbonate → 5-chloro-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1518479Notes

Reaction equation

[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13](CS([O-])(=O)=O)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3].[Cl:21][C:22]1[C:23]([OH:29])=[CH:24][C:25](=[O:28])[NH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:21][C:22]1[C:23]([O:29][CH:13]2[CH2:12][CH2:11][N:10]([C:7]3[N:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][N:6]=3)[CH2:15][CH2:14]2)=[CH:24][C:25](=[O:28])[NH:26][CH:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-(5-propylpyrimidin-2-yl)piperidin-4-ylmethanesulfonate (800 mg, 2.67 mmol), 5-chloro-4-hydroxypyridin-2(1H)-one (389 mg, 2.67 mmol, AK Scientific) and cesium carbonate (2612 mg, 8.02 mmol) in DMF (20 mL) was heated at 120° C. for 6 h. The reaction was cooled to rt, diluted with EtOAc (30 mL), and washed with H2O (3×). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give a yellow solid. The residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) to give the desired product as a yellow solid. MS (ESI) 379 (M+H).

Workup

temperatureThe reaction was cooled to rt
washwashed with H2O (3×)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give a yellow solid
customThe residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-c7e8f0bd9eda4257899b5027cbbc7bec
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232404B2

Reaction notes

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