HCID 66692936, compound → HCID 86670266, compound

HRID 472816Notes

Reaction equation

HRID 472816 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=[C:4]2[N:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:5]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 66692936HCID 66692936, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86670266HCID 86670266, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidin-6-yl)methanol (100 mg, 0.304 mmol) in CH2Cl2 (8 mL) was added PCC (98 mg, 0.455 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue was purified by silica gel chromatography to give the title compound (82 mg, 83%). 1H-NMR (500 MHz, CDCl3) δ ppm 2.52 (3H, s), 2.89 (3H, s), 6.98 (1H, s), 7.33-7.50 (5H, m), 7.60 (2H, d, J=7.9 Hz), 7.91 (2H, dd, J=8.1, 1.4 Hz), 9.80 (1H, s).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a794d449ec8a49e4b984cd0e8b5907ec
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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