HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Azabicyclo[3.1.0]hexane hydrochloride | HCID 22335289 | — |
| Reactant | Avanafil Impurity 37 | HCID 118157672 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid | HCID 117622545 | — |
Reaction Steps
In THF (15 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylic acid (196 mg, 0.55 mmol) and 3-azabicyclo[3.1.0]hexan hydrochloride salt (79 mg, 0.66 mmol). The solution was cooled in an ice bath and triethylamine (167 mg, 1.65 mmol) was then added dropwisely. The reaction was warmed to ambient temperature for 5 h. Then water was added and the reaction mixture was extracted with DCM. The organic phase was dried and concentrated to give a solid. The product was used in the subsequent procedure without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359371B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-2a135e321bc746c083e1e3ff2ea8e92d |
| Source note | uspto-grants-2016_06 |