Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 23512552 | HCID 23512552 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53841856 | HCID 53841856 | 80% |
Reaction Steps
To a suspension of 0.30 g (1.15 mmol) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid in 20 ml CH2Cl2, 0.32 ml (2.3 mmol) triethylamine, 0.17 g (1.15 mmol) 1-hydroxy-benzotriazole and 0.22 g (1.15 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride 0.20 g (1.38 mmol) (3,5-dimethyl-benzyl)-methyl-amine were added. The reaction mixture was stirred for 16 hrs. The reaction mixture was washed with 50 ml 0.5N HCl and 50 ml H2O. The aqueous layers were back extracted with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2) to give 0.36 g (79%) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid (3,5-dimethyl-benzyl)-methyl-amide as a white foam, MS (EI): 391 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06756380B1 |
|---|
| Source dataset | uspto-grants-2004_06 |
|---|
| ORD ID | ord-53c542240fa34467863fa457f519e184 |
|---|
| Source note | uspto-grants-2004_06 |
|---|