Dimethylformamide dimethyl acetal → HCID 178484244, compound

HRID 452972

Reaction equation

HRID 452972 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[C:1]([C:5]1[CH:9]=[C:8](/[N:10]=[CH:13]/[N:14]([CH3:16])[CH3:15])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178441179HCID 178441179, compound

Product 1

HCID 178484244HCID 178484244, compoundYield 99%

Procedure

A mixture of 3-tert-butyl-1H-pyrazol-5-amine (5 g, 36 mmol, Alfa-aesar) and N,N-dimethylformamide dimethylacetal (153 mL, 1078 mmol, Aldrich) was refluxed overnight. The reaction mixture was then cooled, concentrated under reduced pressure and the residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-5% methanol in dichloromethane) to provide 6.9 g (99%) of the title compound. MS (ESI+) m/z 195 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction mixture was then cooled
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ab140c35fa8047ea8097a7d65dc39f06
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Linked notes

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