HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylamine → 6-chloro-N-(2-methyl-4-(N-methylsulfamoyl)phenyl)pyrimidine-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 4-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride | HCID 59446845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-chloro-N-(2-methyl-4-(N-methylsulfamoyl)phenyl)pyrimidine-4-carboxamide | HCID 59446861 | — |
Reaction Steps
A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 400 mg; 1.15 mmol) in THF (20 ml) was treated with methylamine (0.7 ml, 2M in THF; 1.4 mmol) and diisopropylamine (0.4 ml; 2.9 mmol). After stirring at RT for 18 hours the solvent was removed in vacuo and the residue redissolved in DCM and washed with water. The organic extracts were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc. The title product was obtained as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150519B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-0a62b9bc1fa3454b85f4f55cfa4ddb37 |
| Source note | uspto-grants-2015_10 |