methyl 1,4,5,6-tetrahydro-5-pyrimidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】61336

【品名】methyl 1,4,5,6-tetrahydro-5-pyrimidinecarboxylate

【CA登记号】

【分子式】C₆H₁₀N₂O₂

【分子量】142.15768

【元素组成】C 50.69% H 7.09% N 19.71% O 22.51%

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：(IV)

Lithiation of 5-bromopyrimidine (I), followed by addition of CO2 produces pyrimidine-5-carboxylic acid (II). After catalytic hydrogenation of (II), the resultant tetrahydropyrimidine acid (III) is esterified with SOCl2 in MeOH to yield the corresponding methyl ester (IV). Protection of (IV) with triphenylmethyl chloride and DBU affords the N-trityl derivative (V). Then, condensation between the sodium derivative of propionamide oxime (VI) and ester (V) gives rise to the oxadiazole compound (VII). The N-trityl group of (VII) is finally removed with trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Dunbar, P.G.; Durant, G.J.; Fang, Z.; Abuh, Y.F.; El-Assadi, A.A.; Ngur, D.O.; Periyasamy, S.; Hoss, W.P.; Messer, W.S. Jr.; Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J. Med. Chem. 1993, 36, 7, 842.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	38987	5-bromopyrimidine	4595-59-9	C₄H₃BrN₂	详情	详情
(II)	61334	5-pyrimidinecarboxylic acid		C₅H₄N₂O₂	详情	详情
(III)	61335	1,4,5,6-tetrahydro-5-pyrimidinecarboxylic acid		C₅H₈N₂O₂	详情	详情
(IV)	61336	methyl 1,4,5,6-tetrahydro-5-pyrimidinecarboxylate		C₆H₁₀N₂O₂	详情	详情
(V)	61337	methyl 1-trityl-1,4,5,6-tetrahydro-5-pyrimidinecarboxylate		C₂₅H₂₄N₂O₂	详情	详情
(VI)	61338	N'-hydroxypropanimidamide		C₃H₈N₂O	详情	详情
(VII)	61339	5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1-trityl-1,4,5,6-tetrahydropyrimidine		C₂₇H₂₆N₄O	详情	详情

Extended Information