Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl- Chemical Properties

Melting point:

240 °C(Solv: methanol (67-56-1))

Density 

1.90±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

5.97±0.40(Predicted)

Appearance

Off-white to yellow Solid

Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl- Usage And Synthesis

Synthesis

Step 4. Synthesis of N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide An anhydrous tetrahydrofuran (2L) solution of N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide (101 g, 0.40 mol) was treated with N-iodosuccinimide (98.9 g, 0.44 mol, 1.1 eq.) under nitrogen protection and the reaction was stirred at room temperature for 40 min. After completion of the reaction, the solvent was removed by evaporation and the residue was dissolved in dichloromethane (1.5 L) and washed sequentially with sodium sulfite solution (500 mL x 3) and saturated saline (300 mL x 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and recrystallized from methanol to give the title compound as a white powder (122 g, 81% yield, HPLC purity: 98.2%). Retention time (tR): 6.19 min. 1H-NMR (DMSO-d6) δ: 12.65 (broad single peak, 1H), 10.11 (broad single peak, 1H), 7.76 (double peak, 1H), 1.24 (single peak, 9H).

References

[1] Synthesis, 2004, # 8, p. 1203 - 1210
[2] Heterocycles, 1993, vol. 35, # 2, p. 825 - 841
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 13, p. 2325 - 2327
[4] Patent: US2006/223797, 2006, A1. Location in patent: Page/Page column 83-84
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7786 - 7795

Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-(149765-16-2)Related Product Information

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