ChemicalBook CAS DataBase List 2-CHLORO-6-METHOXYPYRAZINE

2-CHLORO-6-METHOXYPYRAZINE synthesis

8synthesis methods

Product Name:2-CHLORO-6-METHOXYPYRAZINE
CAS Number:33332-30-8
Molecular formula:C5H5ClN2O
Molecular Weight:144.56

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

4774-14-5 Synthesis

4774-14-5
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$5.00/1g

33332-30-8
104 suppliers
$7.00/100mg

Yield: 86%

Reaction Conditions:

Stage #1:methanol with sodium hydride in 1,2-dimethoxyethane at 0; for 0.333333 h;Inert atmosphere;
Stage #2:2,6-dichloropyrazine in 1,2-dimethoxyethane at 0 - 45;Inert atmosphere;

Steps:

2-(4-Methoxybenzyloxy)pyrazine (1c)
General procedure: To a suspension of NaH (0.645 g, 26.875 mmol) inanhydrous dimethoxyethane (30 mL) was slowly added dropwise 4-methoxybenzyl alcohol(3.34 mL, 26.907 mmol) at 0 °C over a period of 5 min and stirring continued for 15 min. Then,2-chloropyrazine (2 mL, 22.405 mmol) was added at 0 °C and the mixture heated at 45 °Covernight. The reaction mixture was quenched with slow addition of water (10 mL) andextracted with EtOAc (100 mL), washed with brine, dried over Na2SO4, concentrated underreduced pressure and the resulted crude syrup was purified by flash silica gel columnchromatography (Combiflash Rf) using EtOAc-hexanes (1:9) to obtain 1c (4.650 g, 99%) as awhite solid: mp: 69-71 °C; 1H NMR (CDCl3, 500 MHz) δ 8.25 (s, 1H), 8.11 (d, 1H, J = 3.0 Hz),8.08-8.10 (m, 1H), 7.39 (d, 2H, J = 8.5 Hz), 6.91 (d, 2H, J = 8.5 Hz), 5.32 (s, 2H), 3.81 (s, 3H);13C NMR (CDCl3, 125 MHz) δ 160.1, 159.6, 140.4, 136.6, 136.1, 130.0, 128.3, 113.9, 67.7,55.2; HRMS (ESI) m/z calcd for C12H12N2O2 [M+H]+ 217.09772, found 217.09715

References:

St Hilaire, Valentine R.;Hopkins, William E.;Miller, Yenteeo S.;Dandepally, Srinivasa R.;Williams, Alfred L. [Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 72 - 78] Location in patent:supporting information

4774-14-5 Synthesis

4774-14-5
328 suppliers
$5.00/1g

124-41-4 Synthesis