2-Amino-5-iodo-6-chloro-4-pyrimidinol synthesis

Yield:-

Reaction Conditions:

in N-methyl-acetamide

Steps:

7 2-Amino-5-iodo-6-chloro-4-pyrimidinol
PREPARATION 7 2-Amino-5-iodo-6-chloro-4-pyrimidinol To 1.45 grams (10.0 millimoles) of 6-chloro-isocytosine is added 15 ml. of dimethylformamide (DMF) and 2.27 grams (10.08 millimoles) of N-iodosuccinimide. With protection from external moisture, the mixture is heated on a steam bath for one-hour hour. The resulting brownish red solution is allowed to stand overnight at room temperature with continued exclusion of moisture. The solution is evaporated under reduced pressure and the residual solid azeotroped once with ethanol in vacuo. The resulting solid is triturated with glacial acetic acid. The insoluble solid is collected, washed with a small volume of glacial acetic acid, then with acetone. The solid is re-triturated with glacial acetic acid, collected, washed with acetone and air-dried. Yield, 1.50 g. Evaporation of the combined filtrate in vacuo, trituration of the residue with water, then acetone gives, after collecting and drying, 970 mg. of second-crop material. The first-crop material is crystallized twice from glacial acetic acid to give 540 mg. of 2-amino-5-iodo-6-chloro-4-pyrimidinol which decomposes at >270°, has λmax^0.1N NaOh 236 nm. (ε9,150); 285 nm. (ε6,200) and the infrared absorption below. NH/CH, 3380, 3300, 3190, 3130; O=O/C=C/C=N/NH deformation, 1670_v.s., 1580, 1540; C--N/Other, 1320, 1215, 1010; Other, 910, 755 cm^-1. Analysis Calcd. for: C₄ H₃ CllN₃ O: C, 17.73; H, 1.11; Cl, 13.08; l, 46.83; N, 15.51. Found: C, 18.51; H, 2.24; Cl, 13.38; l, 46.50; N, 14.70.

References:

The Upjohn Company US3932617, 1976, A