Sodium Bicarbonate → tert-Butyl 6-[2-(cyclopropyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

温度

90 °C

6-Trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (11.51 g, 30 mmol) was dissolved in DMF (250 mL) and the yellow solution was purged by bubbling argon (g) through the solution. Potassium acetate (8.83 g, 90 mmol), bis(pinacolato)diboron (8.38 g, 33 mmol), PdCl2 dppf (1.22 g, 1.5 mmol) and dppf (0.83 g, 1.5 mmol) were added and the mixture was purged again with argon. The mixture was then heated to 90° C. for 2 h. Tripotassium phosphate monohydrate (18 g, 78 mmol) was added followed by 2-cyclopropyl-5-bromo-pyrimidine (7.76 g, 39 mmol) and stirring was continued for 5 h at 90° C. The reaction mixture was poured onto saturated sodium bicarbonate solution and extracted several times with ethyl acetate. The ethyl acetate solution was dried over magnesium sulphate, the drying agent filtered off and the filtrate was evaporated. The residue was purified by flash chromatography eluting with ethyl acetate:heptane (1:3) to give 8.1 g (76%) of the title compound as a colourless solid.

1. customthe yellow solution was purged
2. customby bubbling argon (g) through the solution
3. customthe mixture was purged again with argon
4. extractionextracted several times with ethyl acetate
5. dry with materialThe ethyl acetate solution was dried over magnesium sulphate
6. filtrationthe drying agent filtered off
7. customthe filtrate was evaporated
8. customThe residue was purified by flash chromatography
9. washeluting with ethyl acetate:heptane (1:3)

ORDレコード

ord-39052d68033f43fc8db1d4861de917da

出典データセット

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07655664B2