N-methoxy-N,2-dimethyl-3-nitrobenzamide → (4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-methyl-3-nitro-phenyl)-methanone

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Reaction Steps

n-Butyllithium (2.5 M in hexanes, 14.3 mmol) was added dropwise to a suspension of 5-Bromo-4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine (3.7 g, 13.6 mmol) and ethyl ether (75 mL), cooled to −78 C, and stirred for 1 h. N-Methoxy-2,N-dimethyl-3-nitro-benzamide (4.0 g, 17.7 mmol) was added to the reaction mixture, stirred for 2 h, quenched with aqueous NH4Cl (100 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (silica, 3:7 EtOAc:hexanes) provided the title compound as an yellow solid (1.84 g, 38%). MS: 357.5 (MH−); HPLC Rf: 2.0 min. (HPLC method 2); HPLC purity: 100%.

Provenance & Evidence