5-Iodo-2-pyrimidone Chemical Properties

Density 

2.40±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

7.86±0.10(Predicted)

Appearance

Light brown to brown Solid

InChI

InChI=1S/C4H3IN2O/c5-3-1-6-4(8)7-2-3/h1-2H,(H,6,7,8)

InChIKey

PVHCYDBPRLPQMP-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(I)C=N1

5-Iodo-2-pyrimidone Usage And Synthesis

Synthesis

The general procedure for the synthesis of 5-iodo-2-pyrimidinone from 2(1H)-pyrimidinone is as follows: in Example 3, 2-pyrimidinone (6 g, 62.44 mmol) and N-iodosuccinimide (14.7 g, 65.3 mmol) were dissolved in anhydrous DMF (30 ml), and stirred for 48 hr. at room temperature away from light and moisture. After completion of the reaction, the reaction mixture was slowly poured into ether (50 ml) under stirring and the supernatant was removed by decantation. The precipitate was collected by filtration and washed sequentially with acetone and methanol until the filtrate showed light yellow color. After drying under vacuum, the yellow granular product 5-iodo-2(1H)-pyrimidinone was obtained.TLC and spectral analysis showed high purity of the product, but elemental analysis indicated the presence of trace DMF contamination. The final yield was 11.35 g with 77.5% yield.

References

[1] Journal of Medicinal Chemistry, 1985, vol. 28, # 7, p. 904 - 910
[2] Patent: US4895937, 1990, A
[3] Patent: US4782142, 1988, A

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