Reaction #1265390

Reaction equation

sodium hydroxide

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

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

isopropanol

→

sub-titled compound

Yield 35.0%

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

Yield 35.0%

Conditions

Workup

1. 1
   Otherprepared
2. 2
   TemperatureThe resulting mixture was heated
3. 3
   Temperatureto reflux for 6 hours
4. 4
   Temperaturecooled to ambient and
5. 5
   Concentrationconcentrated
6. 6
   workup.ADDITIONThe mixture was diluted with water (20 ml)
7. 7
   Extractionextracted with ethylacetate (20 ml)
8. 8
   Otherthe organic phase was removed
9. 9
   Washwashed with water, brine
10. 10
    Dryingdried (magnesium sulfate)
11. 11
    Concentrationconcentrated
12. 12
    OtherThe residue was purified by flash chromatography (30% ethylacetate/petroleum ether)

Procedure

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).

Source