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【结 构 式】

【分子编号】19813

【品名】8-Cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine

【CA登记号】

【 分 子 式 】C21H31FN4O3

【 分 子 量 】406.5007032

【元素组成】C 62.05% H 7.69% F 4.67% N 13.78% O 11.81%

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:(XI)

The cyclization of N-benzyl-N'-propylurea (I) with cyanacetic acid (II) in hot acetic anhydride gives 6-amino-1-benzyl-3-propyluracil (III), which is nitrosated with NaNO2/acetic acid and reduced with sodium dithionite to yield 5,6-diamino-1-benzyl-3-propyluracil (IV). The cyclization of (IV) with cyclopentylcarbonyl chloride (V) by means of NaOH in refluxing ethanol affords 3-benzyl-8-cyclopentyl-1-propylxanthine (VI), which is acylated with pivaloyl chloride (VII)/Na2CO3 in DMF giving the expected 7-acyl derivative (VIII). The debenzylation of (VIII) by hydrogenation over Pd/C as usual yields 8-cyclopentyl-7-pivaloyl-1-propylxanthine (IX), which is condensed with 1-bromo-3-fluoropropane (X) by means of Na2CO3 in DMF to afford 8-cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine (XI). Finally, this compound is deprotected with NaOH in DMSO/water.

1 Holschbach, M.H.; et al.; A1 adenosine receptor antagonists as ligands for positron emission tomography (PET) and single-photon emission tomography (SPET). J Med Chem 1998, 41, 4, 555.
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) 19803 N-benzyl-N'-propylurea C11H16N2O 详情 详情
(II) 12591 Cyanoacetic Acid; 2-Cyanoacetic acid 372-09-8 C3H3NO2 详情 详情
(III) 19805 6-amino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione C14H17N3O2 详情 详情
(IV) 19806 5,6-diamino-1-benzyl-3-propyl-2,4(1H,3H)-pyrimidinedione C14H18N4O2 详情 详情
(V) 19807 1,4-cyclopentadiene-1-carbonyl chloride C6H5ClO 详情 详情
(VI) 19808 3-benzyl-8-cyclopentyl-1-propyl-3,7-dihydro-1H-purine-2,6-dione C20H24N4O2 详情 详情
(VII) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(VIII) 19810 3-benzyl-8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione C25H32N4O3 详情 详情
(IX) 19811 8-cyclopentyl-7-(2,2-dimethylpropanoyl)-1-propyl-3,7-dihydro-1H-purine-2,6-dione C18H26N4O3 详情 详情
(X) 19812 1-bromo-3-fluoropropane 352-91-0 C3H6BrF 详情 详情
(XI) 19813 8-Cyclopentyl-3-(3-fluoropropyl)-7-pivaloyl-1-propylxanthine C21H31FN4O3 详情 详情
Extended Information