Ethanol → 7-Methyl-8-propyl-[1,2,4]triazolo[1,5-C]pyrimidine
Reaction equation
[CH2:1]([C:4]1[C:5](Cl)=[N:6][CH:7]=[N:8][C:9]=1[CH3:10])[CH2:2][CH3:3].O.[NH2:13][NH2:14].[CH3:15]CO>>[CH3:10][C:9]1[N:8]=[CH:7][N:13]2[N:14]=[CH:15][N:6]=[C:5]2[C:4]=1[CH2:1][CH2:2][CH3:3]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-chloro-6-methyl-5-propyl-pyrimidine (101) (500 mg, 2.93 mmol) and hydrazine monohydrate (880 mg, 17.6 mmol) in EtOH (15 mL) is heated in a sealed tube at 100° C. overnight. On cooling, the solvent is removed and to the residue is added water (15 mL). The solid is filtered and washed with water (5 mL) and ether (10 mL). The solid is then heated in acetic acid (10 mL) in a sealed tube at 110° C. overnight. The excess acetic acid is removed under vacuum. The residue is neutralized with aqueous sodium bicarbonate and then extracted with ethyl acetate. On drying, the solvent is removed to give the product (168).