5-Iodo-3-methyl-2-pyridinamine Chemical Properties

Melting point:

110.2-110.5°C

Boiling point:

303.4±42.0 °C(Predicted)

Density 

1.898±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

solid

pka

5.22±0.49(Predicted)

Appearance

Light yellow to yellow Solid

Sensitive 

Light Sensitive

λmax

296nm(lit.)

InChIKey

WTHKBDPHSGITFJ-UHFFFAOYSA-N

CAS DataBase Reference

166266-19-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

5-Iodo-3-methyl-2-pyridinamine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-3-methyl-5-iodopyridine from 2-amino-3-methyl-5-bromopyridine: 5-bromo-3-methylpyridin-2-amine (2 g, 10.6 mmol), sodium iodide (3.2 g, 21.4 mmol), and copper iodide (0.190 g, 1.06 mmol) were added to dioxane (10 mL), the solution was degassed and tetramethylethane-1,2-diamine (0.803 mL, 1.06 mmol) was added. The mixture was heated at 110 °C overnight. After completion of the reaction, it was cooled to room temperature, water was added and the crude product was extracted with ethyl acetate. The residue was purified by column chromatography to afford 5-iodo-3-methylpyridin-2-amine as a beige solid (2.3 g, 93% yield). Similar to the procedure described in Example 40, 6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.100 g, 0.51 mmol) was reacted with 5- iodo-3-methylpyridin-2-amine (0.119 g, 0.53 mmol) to give, after reversed-phase HPLC purification, the pure 3- (6-amino pyridin-3-yl) -6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.020 g, 13% yield). ES-MS (M + H)+ = 303. Following the method of sulfonylurea formation described in Example 5, 3-(6-amino-5-methylpyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e] [1,3]oxazin-4-one (0.010 g, 0.034 mmol) was coupled with ethyl (5-chlorothiophene-2-sulfonyl)-carbamate (0.048 g, 0.166 mmol) to afford 1-(5-chlorothiophene-2-ylsulfonyl)-3-(5-(6-fluoro-7-(methylamino)-4-oxo-2H-benzo[e][1,3]oxazine -3(4H)-yl)-3-methylpyridin-2-yl)urea (0.016 g, 85% yield).RP-HPLC retention time: 2.7 min; ES-MS (M + H)+ = 526.0; 1H-NMR (DMSO-d6) δ (ppm): 2.2 (s, 3H), 2.8 (s, 3H), 5.6 (s, 2H), 6.2 ( d, 1H), 6.8 (bs, 1H), 7.2 (s, 1H), 7.4 (d, 1H), 7.6 (s, 1H), 7.8 (d, 1H), 8.2 (d, 1H), 9.6 (bs, 1H).

References

[1] Patent: US2006/69093, 2006, A1. Location in patent: Page/Page column 23

5-Iodo-3-methyl-2-pyridinamine(166266-19-9)Related Product Information

• (2-AMINO-5-IODO-PYRIDIN-3-YL)-METHANOL
• 5-Iodo-3-methyl-2-pyridinamine
• 2-(tert-Butyloxycarbonyl-methylamino)-5-iodo-3-methylpyridine
• 5-Iodo-3-methyl-2-methylaminopyridine
• 2-AMINO-5-IODO-PYRIDINE-3-CARBALDEHYDE
• N-(5-IODO-3-METHYL-PYRIDIN-2-YL)-2,2-DIMETHYL-PROPIONAMIDE
• 5-IODO-6-METHYL-2-PYRIDINAMINE
• 2-Amino-5-iodo-4-methylpyridine-3-carbonitrile
• 1-(6-IODO-3,4-DIHYDRO-2H-[1,8]NAPHTHYRIDIN-1-YL)-2,2-DIMETHYL-PROPAN-1-ONE
• N-(5-IODO-3-METHYLPYRIDIN-2-YL)-N-METHYL-2,2-DIMETHYLPROPANAMIDE
• N-(5-IODO-3-METHYL-2-PYRIDINYL)-4-(TRIFLUOROMETHYL)BENZENECARBOXAMIDE
• RARECHEM AN KD 1064
• N-(5-IODO-3-METHYL-2-PYRIDINYL)-2-FURAMIDE
• RARECHEM AN KA 1064
• N-(5-IODO-3-METHYL-2-PYRIDINYL)-2-METHYLBENZENECARBOXAMIDE
• 4-CHLORO-N-(5-IODO-3-METHYL-2-PYRIDINYL)BENZENECARBOXAMIDE
• RARECHEM AN KB 1064
• 2,4-DIBROMO-6-([(5-IODO-3-METHYL-2-PYRIDINYL)AMINO]METHYL)BENZENOL