تفاعل #1265390

معادلة التفاعل

sodium hydroxide

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

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

isopropanol

→

sub-titled compound

المردود 35.0%

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

المردود 35.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared
2. 2
   درجة الحرارةThe resulting mixture was heated
3. 3
   درجة الحرارةto reflux for 6 hours
4. 4
   درجة الحرارةcooled to ambient and
5. 5
   تركيزconcentrated
6. 6
   workup.ADDITIONThe mixture was diluted with water (20 ml)
7. 7
   استخلاصextracted with ethylacetate (20 ml)
8. 8
   أخرىthe organic phase was removed
9. 9
   غسيلwashed with water, brine
10. 10
    تجفيفdried (magnesium sulfate)
11. 11
    تركيزconcentrated
12. 12
    أخرىThe residue was purified by flash chromatography (30% ethylacetate/petroleum ether)

الإجراء التجريبي

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).

المصدر