4-Iodopyrimidin-2-amine Chemical Properties

Boiling point:

364.9±34.0 °C(Predicted)

Density 

2.204±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.27±0.10(Predicted)

Appearance

Off-white to light brown Solid

4-Iodopyrimidin-2-amine Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-amino-4-iodopyrimidine using 2-amino-4-chloropyrimidine as starting material was as follows: 2-amino-4-chloropyrimidine (13.0 g, 100 mmol) was slowly added to 57 wt% aqueous hydriodic acid solution (115 mL, 1.00 mol) at 0 °C. The reaction mixture was stirred continuously for 3 hours at room temperature. Subsequently, the mixture was cooled to 0 °C and the resulting precipitate was removed by filtration. The filter cake was transferred to a pre-cooled aqueous 5 N Na2CO3 solution (200 mL). The aqueous phase was extracted using ethyl acetate (3 × 500 mL), and the combined organic phases were concentrated under reduced pressure to afford 2-amino-4-iodopyrimidine (21.1 g, 95.0 mmol, 95% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.78 (d, J = 5.0 Hz, 1H), 7.02 (br.s, 2H), 7.00 (d, J = 5.0 Hz, 1H). The mass spectrum (ESI, cation mode) showed m/z: 222.1 ([M + H]+).

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 80, p. 364 - 382
[2] Organic Letters, 2014, vol. 16, # 3, p. 708 - 711