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【结 构 式】

【分子编号】29138

【品名】5-(2-ethoxyethyl)-4-hydrazino-6-phenyl-2-pyrimidinamine

【CA登记号】

【 分 子 式 】C14H19N5O

【 分 子 量 】273.33796

【元素组成】C 61.52% H 7.01% N 25.62% O 5.85%

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:(VI)

The alkylation of ethyl benzoylacetate (A) with beta-ethoxyethyl bromide (B) using potassium carbonate in dimethyl formamide at 80 C gives the beta-3-keto ester (I). Condensation of (I) with guanidine hydrochloride (C) using sodium methoxide in tert-butanol at 80 C gives the pyrimidine (II). Protection of the amino group is achieved by tormylation at room temperature with the mixed anhydride (III) from formic and acetic acids. Chlorination with an excess of phosphorus oxychloride at 100 C gives a mixture of (V) and (VIII). The mixture of chloropyrimidines (V, VIII) is stirred at room temperature with excess hydrazi-ne hydrate to give the aminohydrazinopyrimidine (VI). This is heated with ethyl orthoformate in triglyme at 135 C to give the bicyclic compound (VII). This triglyme solution is then heated to 20 C to effect a Dimroth type rearrangement to give SC-33643.

1 Rorig, K.L.; Heilman, R.D.; SC-33643. Drugs Fut 1985, 10, 4, 298.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10004 Ethyl 3-oxo-3-phenylpropanoate; Benzoylacetic acid, ethyl ester 94-02-0 C11H12O3 详情 详情
(D) 21304 Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether 122-51-0 C7H16O3 详情 详情
(B) 29132 ethyl 3-bromopropanoate 539-74-2 C5H9BrO2 详情 详情
(I) 29133 diethyl 2-benzoylpentanedioate C16H20O5 详情 详情
(II) 29134 2-amino-5-(2-ethoxyethyl)-6-phenyl-4-pyrimidinol C14H17N3O2 详情 详情
(III) 29135 Acetyl formyl mixed anhydride C3H4O3 详情 详情
(IV) 29136 5-(2-ethoxyethyl)-4-hydroxy-6-phenyl-2-pyrimidinylformamide C15H17N3O3 详情 详情
(V) 29137 4-chloro-5-(2-ethoxyethyl)-6-phenyl-2-pyrimidinylformamide C15H16ClN3O2 详情 详情
(VI) 29138 5-(2-ethoxyethyl)-4-hydrazino-6-phenyl-2-pyrimidinamine C14H19N5O 详情 详情
(VII) 29139 8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[4,3-c]pyrimidin-5-amine C15H17N5O 详情 详情
(VIII) 29140 4-chloro-5-(2-ethoxyethyl)-6-phenyl-2-pyrimidinylamine C14H16ClN3O 详情 详情
(C) 14790 Guanidine 113-00-8 CH5N3 详情 详情
Extended Information