Water → HCID 86725507, compound

HRID 514378Notes

Reaction equation

HRID 514378 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[C:16]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:16][O:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178429265HCID 178429265, compound

Product 1

HCID 86725507HCID 86725507, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(5-hydroxy-3-methyl-1H-pyrazol-1-yl)pyridine-4-carbonitrile (200 mg, 1 mmol) and K2CO3 (276 mg, 2 mmol) in DMF was added MeI (213 mg, 1.5 mmol) dropwise at −20° C. The mixture was warmed to 0° C. and stirred for 3 h. Water was added, and the reaction mixture was extracted with EtOAc, then washed with water and brine. The organic phase was dried, concentrated, and purified by prep-HPLC to afford the title compound (50 mg). [M+H] Calc'd for C1H10N4O, 215. Found, 215.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washwashed with water and brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-0e9f8c72a3e6457581ca04274fb2a69a
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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