Tetramethyltin → HCID 178501317, compound

Participants

Reaction Steps

In a sealed tube, 4.68 g (9.02 mmol) trans-3-[4-amino-5-(3-benzyloxy-phenyl)-6-bromo-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methylester of Example 103, 2.08 g (1.8 mmol) tetrakistriphenylphosphin palladium and 5.3 ml (38.05 mmol) tin tetramethyl (Fluka, Buchs, Switzerland) are heated under Argon in 20 ml dry N,N-dimethylformamide for 30 h at 100-105° C. bath temperature. The reaction mixture is filtered on hyflo (Hyflo Super Cel®; Fluka, Buchs, Switzerland), and the residue washed thouroughly with N,N-dimethylformamide. The dark filtrate is evaporated at 60° C. to dryness, the residual mass dissolved in hot ethyl acetate and chromatographed on silicagel (hexane-ethyl acetate 25:75). The title compound is obtained as yellow crystals. Analytical HPLC: tR=3.54 min (shorty); ES-MS: m/eo=443; NMR (DMSO-d6): 8.08/s (1H), 7.25-7.5/several m's (6H), 6.99/“d” (1H); 6.90/s (1H); 6.85/“d” (1H); 5.09/s (2H); 5.06/m (1H); 3.64/s (3H); 3.2-3.5/2×m (3H); 2.59/m (2H); 2.18/s (3H).

Provenance & Evidence