Isopropanol → [4-(5-Chloro-thiazol-2-yl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine

反応式

[Cl:1][C:2]1[S:6][C:5]([CH:7]=[CH:8]N(C)C)=[N:4][CH:3]=1.[N+]([O-])([O-])=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:28][C:29]([NH2:31])=[NH2+:30])[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25].[OH-].[Na+].[CH:34](O)(C)C>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:34][N:31]=[C:29]([NH:28][C:20]3[CH:21]=[C:22]([O:26][CH3:27])[C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)[N:30]=2)=[N:4][CH:3]=1

参加物

反応物 4

HCID 3776Isopropanol

HCID 14798Sodium Hydroxide

HCID 72478490[2-(5-Chloro-thiazol-2-yl)-vinyl]-dimethyl-amine

HCID 178419082HCID 178419082、化合物

生成物 1

HCID 58974673[4-(5-Chloro-thiazol-2-yl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine収率 35%

実験手順

To a solution of [2-(5-Chloro-thiazol-2-yl)-vinyl]-dimethyl-amine (450 mg) in isopropanol (10 ml) was added N-(3,4,5 trimethoxyphenyl)guanidinium nitrate (560 mg) (prepared using a procedure similar to that described in WO9719065) and sodium hydroxide (80 mg). The resulting mixture was heated to reflux for 6 hours, then cooled to ambient and concentrated. The mixture was diluted with water (20 ml) and extracted with ethylacetate (20 ml), the organic phase was removed, washed with water, brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography (30% ethylacetate/petroleum ether) to afford the sub-titled compound as an orange solid (260 mg, 35%); IR (solid) 1570, 1508, 1453, 1422 cm−1; 1H NMR (400 Mhz, CDClS) δ 3.8 (3H, s), 3.95 (6H, s), 7.15 (1H, s), 7.50 (1H, m), 7.75 (1H, s), 8.6 (1H, d); MS (ES+) 379.2 (M+1), (ES−) 377.2 (M−1).