Water → HCID 178421992, compound

Participants

Reaction Conditions

Reaction Steps

2.94 g (6.64 mmol) trans-3-[4-amino-5-(3-benzyloxy-phenyl)-6-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methyl ester of Example 104 in 35 ml dry THF are added during 45 min to an ice-cold solution of 0.281 g (7.17 mmol) lithium aluminiumhydride in 30 ml dry THF. The reaction mixture is stirred at 0° C. for additional 20 h. Water is added slowly to the mixture (0.914 ml in 20 min; T≦4° C.), followed by 0.11 ml 4N NaOH. The precipitate is filtered off, the residue on the filter washed with ethyl acetate and water. The filtrate is extracted with ethyl acetate. After drying the organic phase with sodium sulfate, the solvent is evaporated and the residue purified by chromatography (solvent: ethyl acetate-MeOH 95:5). The title compound is obtained as a foam. Analytical HPLC: tR=3.06 min (shorty); ES-MS: m/eo=415; NMR (DMSO-d6): 8.10/s (1H), 7.25-7.5/several m's (6H), 7.25/“d” (1H); 6.95/s (1H); 6.90/1“d” (1H); 5.5-6.0/b (NH2); 5.13/s (2H); 5.04/m (1H); 4.69/t (OH); 3.57/t (2H); 3.15-3.25/m (2H); 2.4-2.5/m (1H); 2.23/s (3H); 2.15-2.25/m (2H).

Provenance & Evidence