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【结 构 式】

【分子编号】64075

【品名】2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine

【CA登记号】

【 分 子 式 】C6H3Cl6N3

【 分 子 量 】329.82624

【元素组成】C 21.85% H 0.92% Cl 64.49% N 12.74%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XIX)

Pyrimidinone (X) is treated with trifluoromethanesulfonic anhydride and Et3N to provide the pyrimidinyl triflate (XV). The triflate group of (XV) is subsequently displaced with cis-1-benzyl-3,5-dimethylpiperazine (XVI) to generate the pyrimidinyl piperazine adduct as a diastereomeric mixture, from which isomer (XVII) can be isolated as the corresponding L-dibenzoyltartrate salt. Removal of the N-benzyl protecting group of (XVII) by transfer hydrogenolysis leads to piperazine (XVIII) (1). This is then coupled with 2-methyl-4,6-bis(trichloromethyl)-[1,3,5]triazine (XIX) to furnish (XX). Finally, dechlorination of (XX) by hydrogenation over Pd/C, followed by acidic ester hydrolysis gives rise to the title compound (1,2).

1 Mylari, B.L.; Oates, P.J.; Zembrowski, W.J.; Beebe, D.A.; Conn, E.L.; Coutcher, J.B.; O'Gorman, M.T.; Linhares, M.C,; Withbroe, G.J.; A sorbitol dehydrogenase inhibitor of exceptional in vivo potency with a long duration of action: 1-(R)-[4-[4-(4,6-Dimethyl[1,3,5]triazin-2-yl)-2R,6S-dimethylpiperazin-1-yl]pyrimidin-2-yl]ethanol. J Med Chem 2002, 45, 20, 4398.
2 Mylari, B.L.; Zembrowski, W.J.; Murry, J.A.; Chu-Moyer, M.Y. (Pfizer Products Inc.); Aminopyrimidines as sorbitol dehydrogenase inhibitors. EP 1185275; US 6414149; WO 0059510 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 64066 (1R)-1-(6-oxo-1,6-dihydro-2-pyrimidinyl)ethyl butyrate C10H14N2O3 详情 详情
(XV) 64071 (1R)-1-(4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyrimidinyl)ethyl butyrate C11H13F3N2O5S 详情 详情
(XVI) 64072 (3R,5S)-1-benzyl-3,5-dimethylpiperazine C13H20N2 详情 详情
(XVII) 64073   C41H46N4O10 详情 详情
(XVIII) 64074   C34H40N4O10 详情 详情
(XIX) 64075 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine C6H3Cl6N3 详情 详情
(XX) 64076 (1R)-1-(4-{(2R,6S)-2,6-dimethyl-4-[4-methyl-6-(trichloromethyl)-1,3,5-triazin-2-yl]piperazinyl}-2-pyrimidinyl)ethyl butyrate C21H28Cl3N7O2 详情 详情
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