ChemicalBook CAS DataBase List 2-AMINO-6-ETHYLPYRIDINE

2-AMINO-6-ETHYLPYRIDINE synthesis

5synthesis methods

Product Name:2-AMINO-6-ETHYLPYRIDINE
CAS Number:21717-29-3
Molecular formula:C7H10N2
Molecular Weight:122.17

45644-21-1
354 suppliers
$10.00/5g

557-20-0
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$14.00/1g

21717-29-3
79 suppliers
$15.00/1g

Yield:-

Reaction Conditions:

1,3-bis[(diphenylphosphino)propane]dichloronickel(II) in 1,4-dioxane;toluene for 16 h;Inert atmosphere;Reflux;

Steps:

14
A mixture of 6-chloro-2-aminopyridine (15.0 g, 1 16 mmol) and [1,3- bis(diphenylphosphino)propane]nickel(II) chloride (5.70 g, 10.5 mmol) in anhydrous 1,4- dioxane (450 mL) was treated with 1.1 M solution of diethylzinc in toluene (225 mL) and the reaction stirred, under a nitrogen atmosphere, at reflux for 16 h. After this time, the reaction was cooled to room temperature, treated with methanol (200 mL) and concentrated under reduced pressure. The resulting residue was diluted in brine (500 L) and extracted with a mixture of 9: 1 methylene chloride/methanol (3 ^x 300 mL). The combined organic layers were dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 6-ethylpyridin-2-amine as a brown gel, which was used in the next step without further purification: NMR (400 MHz, CDC1₃) d 7.36 (t, J = 7.6 Hz, 1 H), 6.53 (d, J= 7.6 Hz, 1H), 6.33 (d, J= 7.6 Hz, 1H), 4.41 (bs, 2H), 2.64 (q, J= 7.6 Hz, 2H), 1.26 (t, J= 7.6 Hz, 3H).

References:

GILEAD SCIENCES, INC.;BLOMGREN, Peter;CURRIE, Kevin, S;KROPF, Jeffrey, E.;LEE, Seung, H.;MITCHELL, Scott, A.;SCHMITT, Aaron, C.;XU, Jianjun;ZHAO, Zhongdong WO2011/112995, 2011, A1 Location in patent:Page/Page column 69