Identification | More | [Name]
5-IODO-6-METHYL-PYRIDIN-2-YLAMINE | [CAS]
75073-11-9 | [Synonyms]
2-AMINO-5-IODO-6-METHYLPYRIDINE 5-IODO-6-METHYL-2-PYRIDINAMINE 5-IODO-6-METHYLPYRIDIN-2-AMINE 5-IODO-6-METHYL-PYRIDIN-2-YLAMINE 6-AMINO-3-IODO-2-PICOLINE AKOS BB-8251 ASISCHEM X26971 VITAS-BB TBB000516 6-Amino-3-iodo-2-methylpyridine | [Molecular Formula]
C6H7IN2 | [MDL Number]
MFCD04138418 | [Molecular Weight]
234.04 | [MOL File]
75073-11-9.mol |
Hazard Information | Back Directory | [Synthesis]
The general procedure for the synthesis of 2-amino-5-iodo-6-methylpyridine from 2-amino-6-methylpyridine is as follows: a mixture of 2-amino-6-methylpyridine (5.40 g), periodic acid (2.28 g), and iodine (5.00 g) was dissolved in a mixture of acetic acid (30 mL), water (6 mL), and sulfuric acid (0.9 mL), and heated to a reaction temperature of 80°C for 3 hr. . After the reaction was completed, the mixture was cooled to room temperature and slowly poured into 100 mL of 10% aqueous sodium bisulfite solution. The aqueous phase was extracted with ether (3 x 100 mL) and the organic phase was combined. The organic phase was washed sequentially with 10% sodium hydroxide solution, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (eluent: ethyl acetate) gave a yellow liquid product. The liquid was further dried under a vacuum pump to induce crystallization to finally obtain 2-amino-5-iodo-6-methylpyridine (4.48 g, 38% yield). The physical properties of the product were as follows: 1H NMR (300 MHz, DMSO-d6) δ 7.60,6.09,6.05,2.38. | [References]
[1] Patent: WO2014/39484, 2014, A1. Location in patent: Page/Page column 50 [2] Journal of Medicinal Chemistry, 2007, vol. 50, # 25, p. 6383 - 6391 [3] Patent: US2002/7066, 2002, A1 [4] Tetrahedron Letters, 2001, vol. 42, # 23, p. 3795 - 3797 [5] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2971 - 2973 |
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