4-Chloro-6-thiophen-2-yl-pyrimidine synthesis
- Product Name:4-Chloro-6-thiophen-2-yl-pyrimidine
- CAS Number:374554-75-3
- Molecular formula:C8H5ClN2S
- Molecular Weight:196.66
1193-21-1
550 suppliers
$14.00/5g
6165-68-0
380 suppliers
$14.00/5g
374554-75-3
9 suppliers
$291.00/250mg
Yield:374554-75-3 62.8%
Reaction Conditions:
with sodium carbonate;bis-triphenylphosphine-palladium(II) chloride in 1,2-dimethoxyethane;water; for 16 h;Reflux;Suzuki Coupling;
Steps:
26.1
4,6-dichloropyrimidine (22.2 g, 149.1 mmol), thiophene-2-boronic acid (20.0 g, 156.3 mmol, 1.05 equiv), Na2C03 (28.8 g, 271.4 mmol, 1.8 equiv) and Pd(PPh3)2Cl2 (2.9 g, 4.2 mmol, 0.03 equiv) were refluxed in dimethoxyethane-water (727:238 mL) mixed solvent system for 16 h. Reaction was monitored by TLC (using ethyl acetate:w-hexane, 1:9).Reaction mixture was cooled and the subject compound was extracted usingdichloromethane. Subject compound was purified by flash chromatography (5% ethyl acetate:w-hexane) to yield 18.4 g of 3 (Yield = 62.8%).1H NMR (CDC13): 8.90 (d, / = 0.9 Hz 1H), 7.79-7.80 (dd, / = 3.9, 1.2 Hz, 1H), 7.58-7.60 (m, 2H), 7.18-7.20 (m, 1H).
References:
WO2011/38234,2011,A2 Location in patent:Page/Page column 33
1193-21-1
550 suppliers
$14.00/5g
6165-68-0
380 suppliers
$14.00/5g
497-19-8
1378 suppliers
$14.00/1KG
374554-75-3
9 suppliers
$291.00/250mg