2-Amino-5-iodopyrimidine

Chemical Properties

cream to brown crystalline powder

Uses

2-Amino-5-iodopyrimidine is used as a reactant in the synthesis of aminopyrimidine and cyclic guanidine amino acids.

Synthesis

General procedure for the synthesis of 2-amino-5-iodopyrimidine from 2-aminopyrimidine: a mixture of 2-aminopyrimidine (2.4 g, 25 mmol, 1.0 eq.) and elemental iodine (2.7 g, 10.7 mmol, 0.43 eq.) was dissolved in 60 mL of glacial acetic acid, followed by the addition of periodate (0.86 g, 3.76 mmol, 0.15 eq.) and 0.5 mL of concentrated sulfuric acid dissolved in 3 mL of water. The reaction mixture was heated to 80 °C and maintained for 24 h under nitrogen protection. Upon completion of the reaction, the reaction mixture was poured into saturated aqueous sodium thiosulfate solution until the solution was clarified (200 mL each time for 3 times) and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography afforded 2-amino-5-iodopyrimidine (1.4 g, 22.2% yield) as a white solid.

References

[1] Heterocycles, 1984, vol. 22, # 5, p. 1195 - 1210
[2] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7468 - 7474
[3] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[4] Synthesis, 1984, # 3, p. 252 - 254
[5] Patent: CN105622638, 2016, A. Location in patent: Paragraph 0362