Ethyl Acetate → 4-(benzyloxy)-N-(3-fluorophenyl)-5-iodopyrimidin-2-amine

HRID 2284754Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([I:15])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C.[F:43][C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][CH:50]=1)[NH2:47]>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[C:14]([I:15])=[CH:13][N:12]=[C:11]([NH:47][C:46]2[CH:48]=[CH:49][CH:50]=[C:44]([F:43])[CH:45]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(benzyloxy)-2-chloro-5-iodopyrimidine (J1, 158 mg) in N-methylpyrrolidone (2.5 mL), 3-fluoroaniline (66 μL) and (1S)-(+)-10-camphorsulfonic acid (159 mg) were added at room temperature, and the mixture was stirred at 60° C. for 2 hours, and then stirred at 80° C. for 7 hours. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with water and 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 to obtain 4-(benzyloxy)-N-(3-fluorophenyl)-5-iodopyrimidin-2-amine (J2, 60 mg) as white solid.

Workup

stirringstirred at 80° C. for 7 hours
temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed successively with water and 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

Sources & evidence

ORD record: ord-fdf3829da7f644bca62100f8858bbc0c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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