Piperidine → HCID 178488444、化合物

Using the method described in Example 30 by employing 1,2-dimethoxy-4-(1-pyrrolidinylvinyl)benzene (freshly prepared before use from 3,4-dimethoxy acetophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.71 g, 7.34 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.50 g, 7.34 mmol), N,N-diisopropylethylamine (1.3 mL, 7.34 mmol), piperidine (1.2 mL, 11.7 mmol), NEt3 (1.3 mL) and SnCl2 (22 mL of a 2 M soln in DMF). In this example the reaction mixture was stirred at room temperature for 48 h after the addition of 2 M SnCl2. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 1.51 g (59%) of 1,2-dimethoxy-4-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzene as a brown colored solid. This material (1.51 g, 4.25 mmol) was dissolved in 5:1 EtOAc/MeOH (90 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (4.30 mL, 4.30 mmol). The solution was left to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAC (2×10 mL), Et2O (3×15 mL) and dried under vacuum at 60° C. to give 0.95 g (34%) of the title compound as a white colored solid. Mp: 268-270° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.57 (s, 3), 3.83 (se 3), 3.89 (s, 3), 4.05 (s, 4), 6.85 (s, 1), 7.13 (d, 1, J=8.4), 7.50-7.54 (m, 2), 11.90 (s, 1), 14.30 (s, 1). MS m/z: 353 (M+1 for free base). Anal. Calcd for C20H24N4O2.HCl.1.25H2O: C, 58.33; H, 6.68; N, 13.61; Cl, 8.51. Found: C, 58.31; H, 6.70; N, 13.54; Cl, 8.49.

1. customwas stirred at room temperature for 48 h
2. customThe residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant

ORDレコード

ord-98a396a7c6a14aad97fb33e3c00aea6f

出典データセット

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06187777B1