Trityl chloride → 1-(2-Triphenylmethyloxyethyl)-5-aminopyrazole-4-carbaldehyde

HRID 349548Notes

Reaction equation

HRID 349548 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[CH:10]=[O:11].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 179620345-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 179619611-(2-Triphenylmethyloxyethyl)-5-aminopyrazole-4-carbaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde (40.2 g) in pyridine (400 ml) was added triphenylmethyl chloride (86.7 g) at room temperature. The mixture was stirred at 60° C. for 5 hours. The reaction mixture was evaporated under reduced pressure and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (3:2) to give 5-amino-1-(2-triphenylmethyloxyethyl)-1H-pyrazole-4-carbaldehyde (62.8 g).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (3:2)

Sources & evidence

ORD record
ord-457674367d9646c887961f2cdeacad81
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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