Ethanol → 1,3,5-Trimethyl-6-(2-(2-diethylaminoethoxy)phenyl)-1H-pyrazolo[4,3-d]pyrimidine-7(6H)-one

HRID 1578805Notes

Reaction equation

HRID 1578805 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[C:5]([N+:10]([O-])=O)[C:4]([CH3:13])=[N:3]1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].[N+]([NH-])([O-])=O.N[NH-].N1C2C=NC=N[C:31]=2[C:30](=O)N=1.Cl.[CH2:39]([N:41]([CH2:44][CH2:45]Cl)[CH2:42][CH3:43])[CH3:40].C(O)C.[O-]CC.[Na+]>C(O)(=O)C>[CH3:1][N:2]1[C:6]2[C:7](=[O:8])[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:40][CH2:39][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[C:30]([CH3:31])=[N:10][C:5]=2[C:4]([CH3:13])=[N:3]1

Participants

10

Reactant 8

HCID 702EthanolHCID 58012-AminophenolHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 168365Hydrazide (H3N21-)2×HCID 2723922Sodium ethoxideHCID 103756241,3-Dimethyl-4-nitro-5-pyrazolecarboxylic acid chlorideHCID 53630237PyrazolopyrimidinoneHCID 178514247HCID 178514247, compound

Product 1

HCID 215585381,3,5-Trimethyl-6-(2-(2-diethylaminoethoxy)phenyl)-1H-pyrazolo[4,3-d]pyrimidine-7(6H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,3-Dimethyl-4-nitro-5-pyrazolecarboxylic acid chloride is reacted with an equimolar quantity of o-aminophenol and the resulting nitroamide is catalytically reduced to the amino amide. Following the method of Example 2, the amino amide is cyclized with acetic acid in an autoclave and the resulting pyrazolopyrimidone is treated with an equimolar amount of diethylaminoethylchloride hydrochloride in absolute ethanol containing two equivalents of sodium ethoxide. 1,3,5-Trimethyl-6-(2-(2-diethylaminoethoxy)phenyl)-1H-pyrazolo[4,3-d]pyrimidine-7(6H)-one is obtained from the reaction mixture.

Sources & evidence

ORD record
ord-3911455a917d407eb578c6f2894bade6
Source dataset
uspto-grants-1976_02
Patent number
US03939161

Reaction notes

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