Pivaloyl chloride → 2-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Steps

To a 100 ml round bottom flask was charged 4.0 g (23.8 mmol) of 2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine dissolved in 50 ml of anhydrous pyridine. To this solution was added 10.2 ml (83 mmol) of trimethylacetyl chloride, and after several minutes a precipitate began forming. The reaction was stirred at RT under a nitrogen atmosphere for 30 min. The volatiles were removed in vacuo, and the residue was dissolved in 1 L of CHCl3, washed twice with 0.1 N HCl, dried over Na2SO4, and removed in vacuo. The crude residue was flash chromatographed on silica gel eluting with a gradient of 100% CHCl3 to 2% MeOH/CHCl3. After collecting the correct fractions, the solvents were removed in vacuo to give 4.4 g (73%) of 2-pivaloyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine as an off-white solid.

Provenance & Evidence