(2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanol → HCID 90051747, compound

HRID 2284702Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([CH2:19][OH:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([CH:19]=[O:20])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanol (E13, 26 mg) in chloroform (2 mL), manganese dioxide (41 mg) was added at room temperature, and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was cooled to room temperature, then the insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 70 to 40% hexane in ethyl acetate) to obtain 2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carbaldehyde (E14, 26 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe insoluble matter was removed by filtration through Cerite
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 70 to 40% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-e4acf1837d3c402fb30479c2782877a0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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