N-Iodosuccinimide → HCID 90051810, compound

HRID 2284814Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:4]([CH3:12])[N:3]=1.[I:13]N1C(=O)CCC1=O.S([O-])(O)=O.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([I:13])=[C:4]([CH3:12])[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2-chloro-6-methyl-N-propylpyrimidin-4-amine (T1, 200 mg) in acetic acid (4 mL), N-iodosuccinimide (485 mg) was added at room temperature, and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogensulfite, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 90-75% hexane in ethyl acetate) to obtain 2-chloro-5-iodo-6-methyl-N-propylpyrimidin-4-amine (T2, 252 mg).

Workup

additionwas added at room temperature
temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with saturated aqueous sodium chloride
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 90-75% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-cac3a6b1bfbc4dbeafb9927a66518f03
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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