4-Phenyl-1H-pyrazol-5-amine → Methyl2-(7-hydroxy-5-methyl-3-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 472824Notes

Reaction equation

HRID 472824 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([CH:16]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:17](OC)=[O:18])(=O)[CH3:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:25][O:24][C:22](=[O:23])[CH2:21][C:16]1[CH:17]([OH:18])[N:10]2[N:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:11]2[NH:12][C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 797034-Phenyl-1H-pyrazol-5-amineHCID 112039Dimethyl acetylsuccinateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 136350318Methyl2-(7-hydroxy-5-methyl-3-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 4-phenyl-1H-pyrazol-5-amine (0.5 g, 3.14 mmol) and dimethyl 2-acetylsuccinate (1.77 g, 9.4 mmol) in xylene (100 mL) was added p-toluenesulfonic acid monohydrate (5 mg, 0.263 mmol). The reaction mixture was heated at reflux under a Dean-Stark trap for 20 hrs. The solid was filtered and washed by hexanes to afford (0.75 g, 80%) of the title compound. 1H-NMR (500 MHz, DMSO-d6) δ ppm 2.38 (3H, s), 3.39 (2H, s), 3.59 (3H, s), 7.33 (1H, S), 7.47 (2H, m), 7.57 (2H, m) 8.13 (1H, S), 11.87 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 20 hrs
  3. filtrationThe solid was filtered
  4. washwashed by hexanes

Sources & evidence

ORD record
ord-b94f7fb4bf0543ce8f3d8d465d17c588
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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