4-(1-piperazinyl)-2,6-di(1-pyrrolidinyl)pyrimidine -Drug Synthesis Database

【结构式】

【分子编号】26075

【品名】4-(1-piperazinyl)-2,6-di(1-pyrrolidinyl)pyrimidine

【CA登记号】

【分子式】C₁₆H₂₆N₆

【分子量】302.42288

【元素组成】C 63.55% H 8.67% N 27.79%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The intermediate pyrimidine (IV) has been obtained as follows: The reaction of 2,4,6-trichloropyrimidine (I) with pyrrolidine in THF gives 6-chloro-2,4-bis(1-pyrrolidinyl) pyrimidine (II), which is condensed with piperazine (III) in pyridine to yield 6-(1-piperazinyl)-2,4-bis(1-pyrrolidinyl)pyrimidine (IV). The methylation of 21-acetoxy-pregna-1,4,9(11),16-tetraene-3,20-dione (V) with methylmagnesium chloride catalyzed by copper propionate, followed by hydrolysis of the acetate group with NaOMe in methanol, gives the 16-alpha-methyl steroid (VI), which is condensed with piperazine intermediate (IV) by means of MeSO2Cl and TEA in acetonitrile, affording the precursor (VII). Finally, this compound is treated with methanesulfonic acid to afford the target compound.

参考文献中间体

合成目标

【1】 Braughler, J.M.; Hall, E.D.; Jacobsen, E.J.; McCall, J.M.; Means, E.D.; THE 21-AMINOSTEROIDS: POTENT INHIBITORS OF LIPID PEROXIDATION FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM TRAUMA AND ISCHEMIA. Drugs Fut 1989, 14, 2, 143.

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)	43734	2,4,6-trichloropyrimidine	3764-01-0	C₄HCl₃N₂	详情	详情
(II)	43735	4-chloro-2,6-di(1-pyrrolidinyl)pyrimidine	111669-15-9	C₁₂H₁₇ClN₄	详情	详情
(III)	10395	1,1,1-Triethoxypropane; 1,1-Diethoxypropyl ethyl ether; Triethyl orthopropionate	115-80-0	C₉H₂₀O₃	详情	详情
(IV)	26075	4-(1-piperazinyl)-2,6-di(1-pyrrolidinyl)pyrimidine		C₁₆H₂₆N₆	详情	详情
(V)	43736	2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate	37413-91-5	C₂₃H₂₆O₄	详情	详情
(VI)	43737	(8S,10R,13S,14S,16R,17S)-17-glycoloyl-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one		C₂₂H₂₈O₃	详情	详情
(VII)	43738	(8S,10R,13S,14S,16R,17S)-17-(2-[4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]acetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one		C₃₈H₅₂N₆O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The condensation of 2,4-bis(1-pyrrolidinyl)-6-(1-piperazinyl)pyrimidine (I) with 3-(bromomethyl)-5-chlorobenzonitrile (II) gives the disubstituted piperazine derivative (III). The partial hydrolysis of the CN group of (III) with methanol/HCl yiedls the iminoether (IV), which is condensed with 4-pyridylcarbonylhydrazide (V) to afford the amidrazone (VI). Finally, this compound is cyclized by heating.

参考文献中间体

合成目标

【1】 van der Goot, H.; et al.; New antioxidants with strong free radical scavenging and xanthine oxidase inhibiting activity. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.243.

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)	26075	4-(1-piperazinyl)-2,6-di(1-pyrrolidinyl)pyrimidine		C₁₆H₂₆N₆	详情	详情
(II)	26076	3-(bromomethyl)-5-chlorobenzonitrile		C₈H₅BrClN	详情	详情
(III)	26077	3-chloro-5-([4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]methyl)benzonitrile		C₂₄H₃₀ClN₇	详情	详情
(IV)	26078	methyl 3-chloro-5-([4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]methyl)benzenecarboximidoate		C₂₅H₃₄ClN₇O	详情	详情
(V)	26079	Isonicotinohydrazide	54-85-3	C₆H₇N₃O	详情	详情
(VI)	26080	N'-[[3-chloro-5-([4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]methyl)phenyl](imino)methyl]isonicotinohydrazide		C₃₀H₃₇ClN₁₀O	详情	详情

Extended Information