HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-[(4-{3-[(5-Bromopyrimidin-2-yl)amino]propyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | 2-{[4-(3-Aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester | HCID 59759007 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 2-[(4-{3-[(5-Bromopyrimidin-2-yl)amino]propyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester | HCID 59758826 | 71.3% |
Reaction Steps
2-{[4-(3-Aminopropyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (5.3 g) synthesized in Example 33 and 5-bromo-2-chloropyrimidine (3.24 g) were dissolved in N-methylpyrrolidone (60 mL), diisopropylethylamine (5.8 mL) was added, and the mixture was stirred at room temperature for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 5:1) to give the title compound (5.65 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08026370B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-842b4122081f48c8b474df76a5c6e813 |
| Source note | uspto-grants-2011_09 |