5-broMo-N,N,6-triMethylpyridin-2-aMine synthesis
- Product Name:5-broMo-N,N,6-triMethylpyridin-2-aMine
- CAS Number:910054-73-8
- Molecular formula:C8H11BrN2
- Molecular Weight:215.09
Yield:910054-73-8 96%
Reaction Conditions:
Stage #1: 5-bromo-6-methyl-pyridin-2-ylaminewith sodium hydride in tetrahydrofuran; for 0.5 h;
Stage #2: methyl iodide in tetrahydrofuran; for 24 h;
Stage #3: with sodium hydride in tetrahydrofuran; for 72 h;
Steps:
3
Preparation 3; (5-Bromo-6-methyl-pyridin-2-yl)-dimethyl-amine; To a solution of 5-Bromo-6-methyl-pyridin-2-ylamine (4 g, 0.021 mole) in tetrahydrofuran (105 mL) was added sodium hydride (60%, 1.2 eq. 1 g). After 30 min, iodomethane (1.56 ml, 1.2 eq.) was added. After an additional 24 h, sodium hydride (60%, 1.2 eq. 1 g). and iodomethane (1.56 ml, 1.2 eq.) were added. The reaction mixture stirred 72 h, and was poured into 1N NaOH, extracted with ethyl ether, dried magnesium sulfated, filtered and concentrated. MPLC biotage chromatography eluting with 2-10% ethyl acetate/hexane provided the title compound as an oil. (4.31 g, 96%). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J=8.7 Hz, 1 H), 6.20 (d, J=8.7 Hz, 1 H), 3.01 (s, 6H), 2.46 (s, 3H).
References:
US2006/211710,2006,A1 Location in patent:Page/Page column 7-8
