HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzylamine → HCID 118157958, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid | HCID 22665572 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 118157958 | HCID 118157958 | 63.2% |
Reaction Steps
In THF (60 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio) pyrimidine-5-carboxylic acid (1.0 g, 2.95 mmol), benzylamine (379 mg, 3.54 mmol) and HATU (1.35 g, 3.54 mmol). DIEA (1 mL, 5.9 mmol) was added dropwisely. The reaction was conducted at ambient temperature for 8 h, followed by addition of water and extraction with DCM. The organic phase was dried over sodium sulfate. Then the solvent was removed by rotary evaporation. The obtained solid was purified by silica gel column chromatography (DCM/methanol=50/1). The product was N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-formamide as a faint yellow solid (800 mg, yield 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359371B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-c5761483eb234cefb9f1328b6fe78713 |
| Source note | uspto-grants-2016_06 |