4-AMINO-2-CHLOROPYRIDINE, N-BOC PROTECTED 98 Chemical Properties

Melting point:

173-175

Boiling point:

282.2±25.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

11.97±0.70(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933399990

4-AMINO-2-CHLOROPYRIDINE, N-BOC PROTECTED 98 Usage And Synthesis

Uses

tert-Butyl (2-Chloropyridin-4-yl)carbamate is a reactant in the preparation of inter-domain stabilizers for allosteric Akt inhibitors.

Synthesis

General procedure for the synthesis of tert-butyl 2-chloropyridine-4-carbamate from 2-chloro-4-aminopyridine and di-tert-butyl dicarbonate: In the presence of 95 mg of 4-dimethylaminopyridine (DMAP), 1.69 g (7.78 mmol, 1 eq.) of di-tert-butyl dicarbonate was dissolved in 50 mL of dichloromethane, and slowly added to a 30 mL solution of dichloromethane containing 1 g (7.78 mmol, 1 eq.) of 2-chloro-4-aminopyridine and 1.19 mL (1.19 mmol, 1.1 eq.) of triethylamine in 30 mL of dichloromethane. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of 100 mL of water and subsequently extracted with dichloromethane. The organic phases were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent ratio varied from 70/30 to 50/50 heptane/ethyl acetate gradient). The resulting oil was crystallized from pentane to give 1.40 g tert-butyl 2-chloropyridine-4-carbamate in 80% yield.

References

[1] Patent: WO2006/53791, 2006, A2. Location in patent: Page/Page column 49-50
[2] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6734 - 6737
[3] Patent: WO2005/33072, 2005, A2. Location in patent: Page/Page column 26
[4] Patent: WO2004/43926, 2004, A1. Location in patent: Page 161
[5] Patent: US2004/102450, 2004, A1. Location in patent: Page/Page column 100

4-AMINO-2-CHLOROPYRIDINE, N-BOC PROTECTED 98(234108-73-7)Related Product Information

• tert-Butyl carbamate
• 4-Amino-2-chloropyridine
• 4-(Boc-amino)pyridine
• tert-butyl 2-chloro-5-nitropyridin-4-ylcarbamate
• 4-AMINO-2-CHLOROPYRIDINE, N-BOC PROTECTED 98