Iodine → 4-amino-1-(4-fluoro-phenyl)-5-iodo-1H-pyrimidin-2-one

HRID 538225Notes

Reaction equation

I([O-])(=O)(=O)=O.[Na+].[I:7]I.[NH2:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:12](=[O:23])[N:11]=1.OS(O)(=O)=O.[O-]S([O-])=O.[Na+].[Na+].[OH-].[Na+]>C(O)(=O)C.O>[NH2:9][C:10]1[C:15]([I:7])=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[C:12](=[O:23])[N:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium metaperiodate (0.21 g, 0.97 mmol) and iodine (0.495 g, 1.95 mmol) were added to a stirred solution of 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one (1 g, 4.87 mmol) in a mixture of acetic acid (12 mL), water (3 mL) and H2SO4 (0.4 mL). The mixture was stirred at 80° C. for 4 hours. The mixture was poured onto an ice-cold 10% aqueous solution of Na2SO3 and then neutralized with a 2N aqueous solution of NaOH to pH 7. A solid was formed, filtered and washed with water and EtOH to yield 4-amino-1-(4-fluoro-phenyl)-5-iodo-1H-pyrimidin-2-one (1.35 g, 84% yield) as a white solid, that was used in the next step without further purification.

Workup

customA solid was formed
filtrationfiltered
washwashed with water and EtOH

Sources & evidence

ORD record: ord-1396e64fdf3b454384243f95e654e176
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865725B2

Reaction notes

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