Sodium hydride → 6-Nitro-1-pyrimidin-5-ylmethyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

5-(Hydroxymethyl)pyrimidine (16.2 g, 147 mmol) was dissolved in 500 mL of CH2Cl2 and cooled to −40° C. MsCl (16.0 g, 140 mmol) was added at 40° C. The mixture was stirred for 1 hour allowing to reach −20° C. The solution was used as such. 6-Nitroindole-1H-indole (35.6 g, 220 mmol) was dissolved in 750 mL of DMF and NaH (50%, 12 g, 250 mmol) was added in portions and the mixture was stirred for 1 hour. The mixture was cooled to −40° C. and the solution of the mesylate was added dropwise. The mixture was allowed to reach room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate (2×). The combined organic layers were washed with water (2×) and brine and dried over Na2SO4. After concentration in vacuo the material was purified by means of column chromatography (silica, heptane/ethyl acetate (1:1)→(1:4)) affording compound the title compound as a yellow solid (14 g, 55 mmol, 39%).

Provenance & Evidence