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(R)-4-isoquinolin-8-yl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
8.15 g
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 90℃; for 3h;Inert atmosphere;
60.1. (R)-4-Isoquinolin-8-yI-2-methyl-piperazine- 1-carboxylic acid tert-butyl ester:To a solution of <strong>[63927-22-0]8-bromoisoquinoline</strong> (5.3g) in toluene (1 20mL) was added successively (R)5 1-N-Boc-2-methylpiperazine (4.84g), tris(dibenzylideneacetone)dipalladium (0) (1.17g), rac2,2-bis(diphenylphosphino)-1 ,1 -binaphthalene (2.38g) and sodium tert-butoxide (3.42g). The reaction mixture was stirred at 90°C under argon for 3h, cooled down and filtered through celite. The plug was washed with EA and the resulting solution was evaporated to dryness. The crude was purified by CC (Biotage, SNAP bOg cartridge, solvent A: Hept;solvent B: EA; gradient in percentB: 15 for 3CV, 15 to 50 over 4CV, 50 for 4CV) to afford 8.1 5g of brown foam. LC-MS (B): tR = 0.70 mm; [M+H]: 328.26.
tert-butyl (R)-4-(4-chloro-5-cyanopyrimidin-2-yl)-2-methylpiperazine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;
To a flask were added 2, 4-dichloropyrimidine-5-carbonitrile (1-a) (3.0 g, 17.24 mmol) , (R) -tert-butyl 2-methylpiperazine-1-carboxylate (12-a) (3.3 g, 16.5 mmol) , DMF (100 ml) and DIEA (8 ml, 46 mmol) . The mixture was stirred at RT for 2 h. To the resulting mixture were added EtOAc and water, and the organic phase was separated and concentrated in vacuo to afford tert-butyl (R) -4- (4-chloro-5-cyanopyrimidin-2-yl) -2-methylpiperazine-1-carboxylate, (15-a) which was used in next step without further purification. MS (ESI) Calc?d for C15H21ClN5O2[M+1]+, 338; found, 338.
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