Cesium carbonate → 2-(4-methyl-5-{(1R)-1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethoxy}-4H-1,2,4-triazol-3-yl)pyrimidine

HRID 2422733Notes

Reaction equation

HRID 2422733 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([C@H:13]([OH:15])[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:16][N:17]1[C:21](S(C)(=O)=O)=[N:20][N:19]=[C:18]1[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:16][N:17]1[C:21]([O:15][C@@H:13]([C:10]2[N:11]=[N:12][N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[N:9]=2)[CH3:14])=[N:20][N:19]=[C:18]1[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 252641052-[4-methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyrimidineHCID 25265528(1R)-1-[2-(3-Methylphenyl)-2H-tetrazol-5-yl]ethanol

Product 1

HCID 252639722-(4-methyl-5-{(1R)-1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethoxy}-4H-1,2,4-triazol-3-yl)pyrimidineYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (1R)-1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanol (251 mg, 1.23 mmol), 2-[4-methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyrimidine (239 mg, 1.00 mmol) and cesium carbonate (911 mg, 2.80 mmol) in N,N-dimethylformamide (10 mL) was stirred at 65° C. for 15 h. After cooling to room temperature, the product was partitioned between ethyl acetate (300 mL) and water (50 mL). The organic layer was washed with water (3×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was concentrated in vacuo. Flash chromatography (silica gel, 2-3% methanol in dichloromethane) yielded the title compound (265 mg, 73%, oil).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe product was partitioned between ethyl acetate (300 mL) and water (50 mL)
  3. washThe organic layer was washed with water (3×50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-a376303708304e4295342da1dc09bd4d
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

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