Triethylamine → 2-Benzyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Hydrazine, (phenylmethyl)-, hydrochloride (1:1)	HCID 14084	—
Reactant	6-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester	HCID 86678217	—
Solvent	Acetonitrile	HCID 6342	—
Product	2-Benzyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester	HCID 136359511	45.3%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Intermediate 5 (250 mg, 0.55 mmol) and benzyl hydrazine hydrochloride (120 mg, 0.61 mmol) were suspended in CH3CN (10 mL) at 0° C., and Et3N (85 μl, 0.61 mmol) was added. The reaction mixture was stirred at 0° C. for 30 mins and then allowed to reach RT and stirred for a further 1 hour. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-100% to yield the title compound as a yellow solid (100 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691826B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-8eadb62c94064794b7d77ec91fd3a388
Source note	uspto-grants-2014_04