Tetrahydrofuran → 3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester

반응식

[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17](C=O)([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:24])[NH:3]1.C1(P(=[CH:44][C:45]([O:47][CH3:48])=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:49]1COCC1>>[CH3:48][O:47][C:45](=[O:46])[CH:44]=[CH:49][C:17]12[CH2:16][CH2:15][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:24])[NH:3][C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:19][CH2:18]1)[CH2:21][CH2:20]2

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HCID 119942814-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

생성물 1

HCID 691483283-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester

실험 절차

4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde (900 mg, 2.73 mmol) was dissolved in 25 mL of THF and methyl (triphenylphosphoranylidene)acetate (1.83 g, 2 eq) was added. The resulting reaction mixture was stirred under reflux for 18 h. It was then cooled to rt and purified by preparative HPLC using a mixture of aqueous acetonitrile to afford 300 mg of the desired product.