HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-(2-hydroxyethyl)-N-methyl-ethanesulfonamide | HCID 18184242 | — |
| Reactant | 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide | HCID 22729415 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide | HCID 86759073 | 34.2% |
Reaction Steps
100 mg 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-benzene sulfonamide was dissolved in 5 ml dry THF. 162 mg of potassium-tert.-butylate and 200 mg of N-(2-hydroxyethyl)-N-methyl-ethanesulfonamide was added and the mixture was heated to reflux for 8 h then cooled to room temperature. Ethyl acetate was added and the precipitated side product was filtered off. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (silica gel; ethyl acetate) to give 45 mg of 4-tert.-butyl-N-{6-[2-(ethanesulfonyl-methyl-amino)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-benzenesulfonamide. LC-MS: tR=5.58 min, [M−1]−=545.54.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06596719B1 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-514d1b28a69341c28f41b8bd3ee2e984 |
| Source note | uspto-grants-2003_07 |