Sodium Iodide → HCID 70896639, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-pyrimidine-2-carboxylic acid tert-butylamide (Example 9, step 1) (950 mg, 3.68 mmol) was dissolved in dioxane (10 ml). Sodium iodide (2.2 g, 14.7 mmol, 4 equiv.), copper(I)iodide (66 mg, 0.74 mmol, 0.2 equiv.) and trans-N,N′-dimethylcyclohexane-1,2-diamine (CAS 67579-81-1) (105 mg, 0.74 mmol, 0.2 equiv.) were added and the mixture was stirred for 16 hours at 100° C. The reaction mixture was extracted with saturated NaHCO3 solution and two times with ethyl acetate. The organic layers were extracted with brine, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography with a 20 g silica gel column and eluting with heptane:ethyl acetate 100:0→0:100. The desired 5-iodo-pyrimidine-2-carboxylic acid tert-butylamide (870 mg, 78% yield) was obtained as a yellow solid, MS: m/e=306.0 (M+H+).

Provenance & Evidence