1,2-Dibromoethane → 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

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Reaction Steps

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (170 mg, 1.01 mmol), 1,2-dibromoethane (0.70 mL, 8.08 mmol), and tetra-n-butylammonium bromide (20 mg) are dissolved in THF (4 mL), and 30% aqueous NaOH (1.01 mL, 7.58 mmol) is added. The mixture is stirred for 24 h at RT, then partitioned between water and EtOAc. The aqueous solution is extracted with additional EtOAc, and the combined organic layers are dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated to dryness. The residue is purified by column chromatography on silica gel, eluting with 2:1-DCM:EtOAc. Fractions containing product are combined and evaporated to dryness to provide 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine as a yellow solid: LC/MS (M+1=276.9). 1H NMR (CDCl3) δ 3.66 (t, 2H, J=8.0 Hz), 4.44 (t, 2H, J=8.0 Hz), 4.92 (br s, 2H), 6.39 (d, 1H, J=4.0 Hz), 6.92 (d, 1H, J=4.0 Hz).

Provenance & Evidence