Ethanol → HCID 21941673, compound

HRID 2216306Notes

Reaction equation

HRID 2216306 reaction equation
Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]([CH3:19])[N:3]=1.CC([O-])=O.[Na+].C(O)C>[Pd].C1(C)C=CC=CC=1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([S:8]([C:7]2[CH:6]=[N:5][C:4]([CH3:19])=[N:3][CH:2]=2)(=[O:9])=[O:10])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 517045Sodium AcetateHCID 21941670HCID 21941670, compound

Product 1

HCID 21941673HCID 21941673, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-5-(4-methoxy-benzenesulfonyl)-2-methylpyrimidine (468 mg, 1.57 mmol), prepared by the method described in example 1 part E, 10% Pd/C (50 mg), NaOAc (128 mg, 1.57 mmol), ethanol (5 mL) and toluene (15 mL) was hydrogenated at 40 psi (Parr Shaker Apparatus) overnight. The mixture was filtered through a pad of silica gel, and washed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide 5-(4-methoxy-benzenesulfonyl)-2-methylpyrimidine (346 mg, 84%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 9.06 (s, 2H), 7.90 (d, J=9.9 Hz, 2H), 7.01 (d, J=9.9 Hz, 2H), 3.88 (s, 3H), 2.80 (s, 3H); ESI MS m/z 265 [(M+H)+, calcd for C12H13N2O3S, 265.1].

Workup

  1. customprepared by the method
  2. customwas hydrogenated at 40 psi (Parr Shaker Apparatus) overnight
  3. filtrationThe mixture was filtered through a pad of silica gel
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

Sources & evidence

ORD record
ord-914c9e476d2c44b29333923fb0687733
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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