Dimethylformamide → HCID 19625728, compound

HRID 238364Notes

Reaction equation

HRID 238364 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[CH3:14][N:15]1[C:19]([NH2:20])=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([NH:20][C:19]1[N:15]([CH3:14])[N:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 19625728HCID 19625728, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl bromide (4.97 g) was added dropwise to a dimethylformamide (15 mL) mixture of 1-methyl-1H-pyrazol-5-amine (2.69 g) and potassium carbonate (4.02 g) at a room temperature, and the obtained solution was then stirred at 70° C. for 3 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1), so as to obtain the title compound (1.54 g) in the form of a light yellow oily substance.

Workup

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (Chromatorex NH, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7594c3ba2e6946bea5423876f674c6ed
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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