Dimethylformamide → HCID 178503591, compound

HRID 487273Notes

Reaction equation

HRID 487273 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([O:14]C)=O)[C:8]([S:16][CH3:17])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[N:19]1[CH:24]=[CH:23][C:22]([C:25](N)=[NH:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=4)=[N:26][C:12](=[O:14])[C:9]3=[C:8]([S:16][CH3:17])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 2776844Pyridine-4-amidine hydrochloride2×HCID 12508124HCID 12508124, compound

Product 1

HCID 178503591HCID 178503591, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 1-cyclopentyl-3-methylthio-5-amino-1H-pyrazole-4-carboxylate (3.0 g, 0.012 mol), 4-pyridine carboxamidine hydrochloride (1.9 g, 0.012 mol), potassium carbonate (1.6 g, 0.012 mol) and DMF (25 ml) were refluxed for 4 hours. Additional 4-pyridinecarboxamidine hydrochloride (1.9 g) and potassium carbonate (1.6 g) were added and the reaction mixture was refluxed for 24 hours. The solution was poured into ice-water, neutralized with acetic acid and the resulting precipitate was collected by filtration and washed with water. Recrystallization of the solid from DMF afforded 0.48 g (12%) of 1-cyclopentyl-3-methylthio-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-one as a white powder, m.p. 272°-274° C. when dried at 110° C. for 16 hours in high vacuum.

Workup

  1. temperaturewere refluxed for 4 hours
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customRecrystallization of the solid from DMF

Sources & evidence

ORD record
ord-a1a18e7185084b7fbdd02a945d78eb71
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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