Hydrochloric Acid → 2-[4-(2-Hydroxyethyl)pyrazol-1-yl]pyridine-4-carbonitrile

HRID 514556Notes

Reaction equation

HRID 514556 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][N:17]=2)[CH:15]=1)(C(C)(C)C)(C)C.Cl.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C1COCC1.O>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][N:14]([C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][N:17]=2)[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 867256612-[4-[2-[Tert-butyl(dimethyl)silyl]oxyethyl]pyrazol-1-yl]pyridine-4-carbonitrile

Product 1

HCID 867256632-[4-(2-Hydroxyethyl)pyrazol-1-yl]pyridine-4-carbonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]pyrazol-1-yl]pyridine-4-carbonitrile (1.2 g, 3.6 mmol) in THF (15 mL) at 0° C. was added 3N HCl (5 mL). The reaction mixture was then stirred for 2 hours at room temperature. Cool to 0° C., added ethyl acetate, water and acidified with NaHCO3 to pH=8. The mixture was then extracted with ethylacetate, concentrated to afford the title compound (700 mg, 91%). [M+H] Calc'd for C11H10N4O, 215. Found, 215.

Workup

  1. temperatureCool to 0° C.
  2. extractionThe mixture was then extracted with ethylacetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-40445f82da574d88ac98469830096aa8
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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