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Reference Example 128 Triphenylphosphine (14.3 g) was added to a THF (190 ml) solution containing tert-butyl S,2S)-2-hydroxycyclohexyl) carbamate (10.0 g), followed by ice cooling. Diethyl azodicarboxylate (40% in toluene) (24.3 g) and DPPA (15.3 g) were added dropwise to the reaction solution, followed by stirring at room temperature for 1 hour. The reaction solution was left overnight. The solvent was distilled away under reduced pressure. Water was added and then a 20% sodium hydroxide aqueous solution was added. Then, the organic layers were collected. Water (30 ml) was added to the obtained organic layers, followed by heating to 60 C. A THF (40 ml) solution containing triphenylphosphine (14.3 g) was added dropwise, followed by reflux for 2.5 hours. The solvent was distilled away under ordinary pressure. Toluene was added and the pH was adjusted with 3M hydrochloric acid to pH=1 or less. Then, the resulting aqueous layers were collected, ethyl acetate was added, and the pH was adjusted with a 20% sodium hydroxide aqueous solution to pH 12. The organic layers were collected and dried over anhydrous sodium sulfate. Light yellow oily matter of tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate (5.24 g) was thus obtained.
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 45℃; for 0.333333h;
2,4-Dichloropyrimidine-5-carbonitrile (4.46 g, 25.6 mmol) was dissolved in 100 mL DMF. To it were added tert-butyl ((lS,2R)-2-aminocyclohexyl)carbamate (4.99 g, 23.3 mmol) and DIEA (6.1 mL, 35. 0 mmol). The mixture was stirred at 45°C for 20 m to afford two coupling product in about equal amount in quantitative yield. The mixture was concentrated in vacuo, diluted with EtOAc, washed with brine twice, dried, concentrated and subjected to flash column to separate tert-butyl ((lS,2R)-2-((4-chloro-5-cyanopyrimidin-2- yl)amino)cyclohexyl)carbamate.
methyl 5-[[(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl]amino]pyrazolo[1,5-a]pyrimidine-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
46%
at 90.0℃; for 0.5h;Sealed tube; Microwave irradiation;
A microwave vial was charged with <strong>[1224944-51-7]methyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate</strong> (500 mg, 2.36 mmol), tert-butyl N-[(1S,2R)-2-aminocyclohexyl]carbamate (506 mg, 2.36 mmol), and methanol (4.7 mL). The vial was sealed and stirred at 90 C for 30 min in the microwave, resulting in a suspension. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography (0-100% isopropyl acetate/heptane) to afford methyl 5- [[(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl]amino]pyrazolo[1,5-a]pyrimidine-3- carboxylate (420.2 mg, 1.08 mmol, 46% yield) as a white solid. MS: m/z = 390 (M+1).
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