Sodium sulfate decahydrate → HCID 89768198, compound

HRID 591504Notes

Reaction equation

HRID 591504 reaction equation
[CH3:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[CH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([C:13]([F:16])([F:14])[F:15])[N:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 10609709Ethyl 4-methyl-2-(trifluoromethyl)pyrimidine-5-carboxylateHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 89768198HCID 89768198, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of ethyl 4-methyl-2-(trifluoromethyl)pyrimidine-5-carboxylate (122.4 mg) in toluene (5.1 mL) was added diisobutylaluminum hydride (1.0 mol/L in hexane, 1.150 mL) at 0° C. The mixture was stirred at 0° C. under nitrogen atmosphere for 2.5 h, and then at room temperature for 2 h. To the mixture was added diisobutylaluminum hydride (1.0 mol/L in hexane, 0.58 mL) again at 0° C. and the mixture was stirred at 0° C. for 2 h. To the mixture was added sodium sulfate decahydrate (556 mg), and the mixture was stirred at room temperature overnight. The mixture was filtered through on the pad of Celite®. The filtrate was concentrated in vacuo to give the title compound (97.6 mg).

Workup

  1. waitat room temperature for 2 h
  2. stirringthe mixture was stirred at 0° C. for 2 h
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationThe mixture was filtered through on the pad of Celite®
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-464c8003ef5d4dfa89dd122143c0839a
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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