Potassium Hydroxide → N-tert-butyl-4-ethynylpyrimidin-2-amine

Participants

Reaction Steps

A solution of 2-tert-butylamino-4-[trimethylsilylethynyl]pyrimidine (from Example 2) in CH3OH (150 mL) was treated with a solution of KOH (30 mg) in CH3OH (5 mL). After 30 min, additional KOH (30 mg) in CH3OH (5 mL) was added. After a further 30 min, the mixture was concentrated and the residue was diluted with hexanes and loaded directly onto a short pad of SiO2. The product was eluted with 10% EtOAc in hexanes to provide the crude product as a light brown oil (18.6 g, 90% for 2 steps), which was used without further purification. TLC: Rf=0.29. IR: 3294 (m), 2965 (m), 2114 (w), 1571 (s). 1H NMR: 8.23 (d, J=5.0 Hz, 1H), 6.60 (d, J=5.0 Hz, 1H), 5.20 (s, 1H), 3.15 (s, 1H), 1.43 (s, 9H). 13C NMR: 161.97, 157.99, 149.87, 112.63, 81.71, 78.72, 51.06, 28.80.

Provenance & Evidence