Hydrochloric Acid → 1-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-1H-[1,2,3]triazole-4-carbaldehyde

HRID 403498Notes

Reaction equation

HRID 403498 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:6]=[N:7][N:8]([C:10]2[CH:29]=[CH:28][C:13]([CH2:14][C:15]3[C:16]([CH2:26][CH3:27])=[N:17][N:18]4[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[N:20][C:19]=34)=[CH:12][CH:11]=2)[CH:9]=1)C.Cl>O1CCOCC1>[CH2:26]([C:16]1[C:15]([CH2:14][C:13]2[CH:28]=[CH:29][C:10]([N:8]3[CH:9]=[C:5]([CH:4]=[O:3])[N:6]=[N:7]3)=[CH:11][CH:12]=2)=[C:19]2[N:20]=[C:21]([CH3:25])[CH:22]=[C:23]([CH3:24])[N:18]2[N:17]=1)[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 683789103-[4-(4-Diethoxymethyl-[1,2,3]triazol-1-yl)-benzyl]-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 866717571-[4-(2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-1H-[1,2,3]triazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-[4-(4-diethoxymethyl-[1,2,3]triazol-1-yl)-benzyl]-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (21) (2.19 g, 5.04 mmol) and 4N HCl (50 ml, 200 mmol) in 30 ml of dioxane was stirred at r.t. for 2 h. The reaction mixture was quenched with sat aq NaHCO3 and extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Na2 SO4, filtered and concentrated under HV.

Workup

  1. customThe reaction mixture was quenched with sat aq NaHCO3
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. customdried over anhydrous Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated under HV

Sources & evidence

ORD record
ord-6ff3edd3638849ecb3dd584eebe8d414
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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