反応 #1265390

反応方程式

sodium hydroxide

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

N-(3,4,5 trimethoxyphenyl)guanidinium nitrate

isopropanol

→

sub-titled compound

収率 35.0%

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

収率 35.0%

反応条件

後処理

1. 1
   その他prepared
2. 2
   温度The resulting mixture was heated
3. 3
   温度to reflux for 6 hours
4. 4
   温度cooled to ambient and
5. 5
   濃縮concentrated
6. 6
   workup.ADDITIONThe mixture was diluted with water (20 ml)
7. 7
   抽出extracted with ethylacetate (20 ml)
8. 8
   その他the organic phase was removed
9. 9
   洗浄washed with water, brine
10. 10
    乾燥dried (magnesium sulfate)
11. 11
    濃縮concentrated
12. 12
    その他The residue was purified by flash chromatography (30% ethylacetate/petroleum ether)

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).

出典