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【结 构 式】

【分子编号】65104

【品名】2-amino-6-ethynyl-4-quinazolinylamine; 6-ethynyl-2,4-quinazolinediamine

【CA登记号】

【 分 子 式 】C10H8N4

【 分 子 量 】184.20048

【元素组成】C 65.21% H 4.38% N 30.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Palladium-catalyzed coupling of 2,4-diamino-6-iodoquinazoline (I) with trimethylsilyl acetylene (II) affords the silylethynyl quinazoline (III). Subsequent treatment of (III) with tetrabutylammonium fluoride leads to the desilylated acetylene compound (IV).

1 Vaidya, C.M.; Wright, J.E.; Rosowsky, A.; Synthesis and in vitro antitumor activity of new deaza analogues of the nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Nalpha-hemiphtaloyl-L-ornithine (PT523). J Med Chem 2002, 45, 8, 1690.
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) 65105 2-amino-6-iodo-4-quinazolinylamine; 6-iodo-2,4-quinazolinediamine C8H7IN4 详情 详情
(II) 51602 1-Propyne C3H4 详情 详情
(III) 65103 2-amino-6-[2-(trimethylsilyl)ethynyl]-4-quinazolinylamine; 6-[2-(trimethylsilyl)ethynyl]-2,4-quinazolinediamine C13H16N4Si 详情 详情
(IV) 65104 2-amino-6-ethynyl-4-quinazolinylamine; 6-ethynyl-2,4-quinazolinediamine C10H8N4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Condensation between phthaloyl ornithine methyl ester (V) and 4-iodobenzoic acid (VI), via activation with isobutyl chloroformate, furnishes the iodobenzamide (VII). Subsequent coupling of iodo amide (VII) with the ethynyl quinazoline (IV) employing Pd(PPh3)4 and CuI leads to the disubstituted acetylene (VIII). Catalytic hydrogenation of the triple bond in the presence of Pd/C affords (IX). Then, basic hydrolysis of phthalimido ester (IX) by means of Ba(OH)2 produces the target compound.

1 Vaidya, C.M.; Wright, J.E.; Rosowsky, A.; Synthesis and in vitro antitumor activity of new deaza analogues of the nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Nalpha-hemiphtaloyl-L-ornithine (PT523). J Med Chem 2002, 45, 8, 1690.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 65104 2-amino-6-ethynyl-4-quinazolinylamine; 6-ethynyl-2,4-quinazolinediamine C10H8N4 详情 详情
(V) 42875 methyl (2S)-2-amino-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate C14H16N2O4 详情 详情
(VI) 53872 4-iodobenzoic acid 619-58-9 C7H5IO2 详情 详情
(VII) 65108 methyl (2S)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[(4-iodobenzoyl)amino]pentanoate C21H19IN2O5 详情 详情
(VIII) 65107 methyl (2S)-2-({4-[2-(2,4-diamino-6-quinazolinyl)ethynyl]benzoyl}amino)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate C31H26N6O5 详情 详情
(IX) 65106 methyl (2S)-2-({4-[2-(2,4-diamino-6-quinazolinyl)ethyl]benzoyl}amino)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate C31H30N6O5 详情 详情
Extended Information