2-[(6-amino-2-chloro-9H-purin-9-yl)methoxy]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】39968

【品名】2-[(6-amino-2-chloro-9H-purin-9-yl)methoxy]-1-ethanol

【CA登记号】

【分子式】C₈H₁₀ClN₅O₂

【分子量】243.6526

【元素组成】C 39.44% H 4.14% Cl 14.55% N 28.74% O 13.13%

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：(VII)

The reaction of benzonitrile (I) with refluxing ethylene glycol (II) gives ethylene glycol monobenzoate (III), which is chloromethylated with formaldehyde and dry HCl in CH2Cl2 affording 1-benzoyloxy-2-chloromethoxyethane (IV). The condensation of (IV) with 2,6-dichloropurine (V) by means of triethylamine in DMF yields 2,6-dichloro-9-(2-benzoyloxyethoxymethyl)purine (VI), which is aminated and debenzoylated by treatment with NH3 in methanol at 95 C in a pressure vessel giving 2-chloro-9-(2-hydroxyethoxymethyl)adenine (VII). The Sandmeyer reaction of (VII) with NaNO2 in acetic acid affords 2-chloro-9-(2-hydroxyethoxymethyl)hypoxanthine (VIII), which is finally amonolyzed with ammonia in methanol at 125 C in a pressure vessel.

参考文献中间体

合成目标

【1】 Schaeffer, H.J.; et al.; 9-(2-Hydroxyethoxy)guanine activity aganist viruses of the herpes group. Nature 1978, 272, 583-585.
【2】 Castaner, J.; Hillier, K.; Acycloguanosine. Drugs Fut 1978, 3, 11, 788.
【3】 Schaeffer, H.J. (Glaxo Wellcome plc); Purine derivs.. US 4294831 .

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)	25904	benzonitrile	100-47-0	C₇H₅N	详情	详情
(II)	11295	Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol	107-21-1	C₂H₆O₂	详情	详情
(III)	39965	2-hydroxyethyl benzoate		C₉H₁₀O₃	详情	详情
(IV)	39966	2-(chloromethoxy)ethyl benzoate		C₁₀H₁₁ClO₃	详情	详情
(V)	25254	2,6-dichloro-9H-purine	5451-40-1	C₅H₂Cl₂N₄	详情	详情
(VI)	39967	2-[(2,6-dichloro-9H-purin-9-yl)methoxy]ethyl benzoate		C₁₅H₁₂Cl₂N₄O₃	详情	详情
(VII)	39968	2-[(6-amino-2-chloro-9H-purin-9-yl)methoxy]-1-ethanol		C₈H₁₀ClN₅O₂	详情	详情
(VIII)	39969	2-chloro-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol		C₈H₉ClN₄O₃	详情	详情

Extended Information