Lithium Hydroxide → 6-(7H-Pyrrolo[2,3-d]pyrimidin-5-yl)-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

As shown in FIG. 7—step iii, a mixture of compound 1032 (0.18 g), 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (compound 1005, 0.20 g), tetrakis(triphenylphosphine) palladium (50 mg), and 2N sodium carbonate (0.8 mL) in DME (5 mL) was heated at 90° C. overnight. Saturated aqueous lithium hydroxide (2 mL) was added and the reaction was heated at 60° C. for 1 hour. The reaction mixture was diluted with EtOAc and washed with brine. The organics were dried over sodium sulfate, concentrated, and purified by chromatography (SiO2, 50% ethyl acetate/hexane) to afford 6-(7H-Pyrrolo[2,3-d]pyrimidin-5-yl)-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (compound 1033, 81.6 mg).

Provenance & Evidence