HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Fluorobenzylamine → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Fluorobenzylamine | HCID 67326 | — |
| 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-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid | HCID 71235039 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide | HCID 90169457 | 52.3% |
Reaction Steps
4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (300 mg, 0.88 mmol) and 4-fluorobenzylamine (165 mg, 1.32 mmol) were dissolved in 20 mL THF, DIEA (0.45 mL, 2.64 mmol) was added dropwise, HATU (401 mg, 1.06 mmol) was added under ice-water-bath, reacted at room temperature for 4 h, to the reaction solution was added 100 mL of water, then extracted with dichloromethane, dried with anhydrous sodium sulfate, dried by rotation, the solid was separated with silica gel separation (dichloromethane:methanol=100:1) to obtain a white solid 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(4-fluorobenzyl)pyrimidine-5-carboxamide 206 mg, yield 52%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08980904B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-3378e5d8212b46b7a99baa70c31bda75 |
| Source note | uspto-grants-2015_03 |