Analyzing the synthesis route of 129779-30-2

129779-30-2, The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.129779-30-2,(3R,5S)-rel-tert-Butyl 3,5-dimethylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

173 2-flH-Ihdazol-4-yl)-4-morpholin-4-yl-6-((2S.6R)-2A6-trimethyl-piperazin-l- ylmethylVthieno[3 ,2-dlpyrimidineTo (66) (1.5g) in ethanol (3OmL) was added sodium borohydride (Ig). After 4 h the reaction mixture was quenched with brine and the resulting solid was collected by filtration, and air dried to furnish 168 (2-chloro-4-morpholin-4-yl- thieno[3,2-d]pyrimidin-6-yl)-rnethanol (1.42g).To a solution of 168 (1.42g) in toluene (14ml), warmed to 400C, was added phosphorous tribromide (0.16ml). The resulting mixture was then heated to 1000C for 6 h, was cooled, diluted with chloroform, washed with brine, and dried (MgSO4). The solvent was removed in vacuo to yield 6-bromomethyl-2-chloro-4-morpholin-4- yl-thieno[3,2-d]pyrimidine, 169 (1.4Og). EPO A mixture of (3R,5S)-3,5-dimethyl-piperazine-l-carboxylic acid tert-buty ester (0.92g), 6-bromomethyl-2-chloro-4-mophiholin-4-yl-thieno[3,2-d]pyrimidine (Ig) and potassium carbonate (1.59g) in MeCN (10ml) was heated to reflux for 5 days. The reaction mixture was subsequently cooled, diluted with chloroform, washed with brine and dried (MgSO4), and the solvent was removed in vacuo. The residue was purified by flash column chromatography to yield (3S,5R)-4-(2-chloro- 4-mophiholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-3,5-dimethyl-piperazine-l- carboxylic acid tert-butyl ester, 170 (1.2g). Treatment of this compound with HCl in DCM/MeOH produced 2-chloro-6-(2S,6R)-2,6-dimethyl-piperazin- 1 -ylmethyl)-4- mophiholin-4-yl-thieno[3,2-d]pyrimidine, 171, which was then methylated using 37% formaldehyde solution and sodium borohydride in MeOH, furnishing 172. 1H NMR (400MHz, CDCl3) 1.17 (6H, d), 1.92 (2H, t), 2.3 (3H, s), 2.73 (2H, d), 2.83 (2H, m), 3.95 (4H, m), 4.03 (4H, m), 4.18 (2H, s), 7.36 (IH, s), 7.48 (IH, t), 7.56 (IH, d), 8.26 (IH, d), 9.00 (IH, s), 10.40 (IH, br m); MS (ESI+) 478 (MH+).

129779-30-2, The synthetic route of 129779-30-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PIRAMED LIMITED; WO2006/46031; (2006); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics