تفاعل #635099

معادلة التفاعل

5-bromo-2-phenyl-pyrimidine

4-amino-piperidine-1-carboxylic acid tert-butyl ester

N,N-diethylsalicylamide

K3PO4

→

title compound

المردود 47.8%

4-(Pyrimidin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

المردود 47.8%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was removed under reduced pressure
2. 2
   أخرىthe crude reaction product
3. 3
   استخلاصextracted from water (300 mL) and 25% NH4OH (30 mL) with ethyl acetate (3×300 mL)
4. 4
   تجفيفThe combined organic phases were dried over Na2SO4
5. 5
   تركيزconcentrated by evaporation under reduced pressure
6. 6
   أخرىthe crude material purified by silica column chromatography
7. 7
   غسيلeluting with a gradient of heptane/ethyl acetate (4:1→1:1)

الإجراء التجريبي

A mixture of 5-bromo-2-phenyl-pyrimidine (3.50 g, 14.89 mmol, 1.0 equiv), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (4.48 g, 22.33 mmol, 1.5 equiv), copper(I) iodide (0.28 g, 1.49 mmol, 0.1 equiv), N,N-diethylsalicylamide (0.58 g, 2.98 mmol, 0.2 equiv) and K3PO4 (3.16 g, 14.89 mmol, 1.0 equiv) in degassed DMF (30 mL) was heated under Ar to 90° C. for 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from water (300 mL) and 25% NH4OH (30 mL) with ethyl acetate (3×300 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluting with a gradient of heptane/ethyl acetate (4:1→1:1) to provide 1.98 g (38%) of the title compound. MS (ESI): 377.1 [M+Na]+.

المصدر