HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl 4-(bromomethyl)benzoate | HCID 256687 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 2-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester | HCID 59758871 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester | HCID 67397350 | 55.4% |
Reaction Steps
2-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (3.0 g) synthesized in Example 265-1 and 4-(bromomethyl)benzoic acid methyl ester (2.0 g) were dissolved in N,N-dimethylformamide (37 mL), potassium tert-butoxide (0.91 g) was added thereto, 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=5:1) to give the title compound (2.2 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-aa6aea258a0e441f81eb3824768ab9a9 |
| Source note | uspto-grants-2011_09 |