3,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester → HCID 66601738, compound

HRID 604306Notes

Reaction equation

HRID 604306 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([CH3:24])=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:16]=1[CH3:17])=O)C>O1CCCC1>[CH3:24][C:13]1[C:12]([CH2:10][OH:9])=[C:16]([CH3:17])[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:14]=1

Participants

4

Reactant 2

HCID 98562563,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 66601738HCID 66601738, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Suspend lithium aluminum hydride (0.359 g, 9.46 mmol) in tetrahydrofuran (25 mL) at −10° C. and add 3,5-dimethyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester (1.160 g, 4.73 mmol) dropwise in tetrahydrofuran (5 mL). Allow the mixture to warm to 25° C. and stir for 4 hr. Cool the mixture to 0° C. then quench carefully with saturated sodium sulfate solution (1 mL). Allow the mixture to stir at room temperature for 2 hr. then filter off the precipitate, dry the solution and concentrate to give (3,5-dimethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-methanol as a yellow solid (0.821 g, 86%).

Workup

  1. customat −10° C.
  2. temperatureCool the mixture to 0° C.
  3. customthen quench carefully with saturated sodium sulfate solution (1 mL)
  4. stirringAllow the mixture to stir at room temperature for 2 hr
  5. filtrationthen filter off the precipitate
  6. customdry the solution
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-5b30229dff8c4c0889fed0bd1d6798ca
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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