HuagongsheHuagongshe Chemistry Print Report · For research reference only
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 | US09023855B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-9d53a47cd66a473a987b976aa878eadc |
| Source note | uspto-grants-2015_05 |