Chloroform → 1-cyclopentyl-6-(2-ethoxyphenyl)-3-ethyl-2H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 619141

Reaction equation

HRID 619141 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)[CH3:18].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>CS(O)(=O)=O.C(Cl)Cl>[CH:1]1([N:6]2[C:10]3=[N:11][C:22]([C:21]4[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=4[O:19][CH2:17][CH3:18])=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 11950Benzaldehyde, 2-ethoxy-HCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 1784661681-cyclopentyl-6-(2-ethoxyphenyl)-3-ethyl-2H-pyrazolo[3,4-d]pyrimidin-4-oneYield 45%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9 mmol), o-ethoxybenzaldehyde (2.7 g, 18 mmol), methanesulfonic acid (5 drops), and xylenes (50 ml) was refluxed for 48 hours. The reaction mixture was stripped to dryness, and treated with 10% K2CO3 and CHCl3 (100 ml). The layers were separated and the aqueous layer was extracted with chloroform (2×100 ml). The organic layers were combined, and concentrated in vacuo. The dark oil thus obtained was dissolved in CH2Cl2 (30 ml) and combined with silica gel (30 g). The preloaded silica gel was placed on a silica gel column and eluted with Et2O/hexanes (20/80) to Et2O (100%) to afford 1.41 g (45%) of 1-cyclopentyl-3-ethyl-6-(2-ethoxyphenyl)-pyrazolo[3,4-d]pyrimidin-4-one, m.p. 146-147° C.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with chloroform (2×100 ml)
  4. concentrationconcentrated in vacuo
  5. customThe dark oil thus obtained
  6. washeluted with Et2O/hexanes (20/80) to Et2O (100%)

Sources & evidence

ORD record
ord-897d4a8b33a743f893080ddd243b84a0
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Linked notes

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