Sodium Carbonate → (R)-tert-butyl-3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate

온도

90 °C

A mixture of (R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (1) (2.0 g, 4.66 mmol), 4-phenoxyphenylboronic acid (1.3 g, 6.06 mmol), Pd(dppf)Cl2 (190 mg, 0.23 mmol) and Na2CO3 (1.9 g, 14.0 mmol) in DME (35.0 mL) and H2O (15.0 mL) was heated at 90° C. under N2 atmosphere overnight. After cooled down to r. t., the reaction mixture was diluted with water (50.0 mL) and DCM (50.0 mL). The layers were separated and the aqueous phase was extracted with DCM (25 mL×1). Combined organic phases were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product which was purified by column chromatographic (silica gel, 0-80% ethyl acetate in petroleum ether (“PE”) with DCM (1:1)) to afford (R)-tert-butyl-3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (2) (1.3 g, 60% yield) as a yellow solid. LC-MS (ESI): (M+1) 472.1.

1. temperatureAfter cooled down to r
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with DCM (25 mL×1)
4. washCombined organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customto obtain the crude product which
8. customwas purified by column chromatographic (silica gel, 0-80% ethyl acetate in petroleum ether (“PE”) with DCM (1:1))

ORD 기록

ord-74518ca87f89489b9a9603bec0305fcd

출처 데이터셋

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09062058B2