Methylamine → 5-iodo-N2-methyl-N4-propylpyrimidine-2,4-diamine

HRID 2284722Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([I:12])=[CH:4][N:3]=1.[CH3:13][NH2:14]>O1CCCC1.CO>[I:12][C:5]1[C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[N:7][C:2]([NH:14][CH3:13])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-iodo-N-propylpyrimidin-4-amine (F1, 46.3 mg) in tetrahydrofuran (0.5 mL), a 9.8 mol/L solution of methylamine in methanol (0.5 mL) was added at room temperature, the reaction vessel was sealed, and then by using a microwave reaction system, the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 40 to 27% hexane in ethyl acetate) to obtain 5-iodo-N2-methyl-N4-propylpyrimidine-2,4-diamine (F222, 32.4 mg) as white solid.

Workup

customthe reaction vessel was sealed
customa microwave reaction system
temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 40 to 27% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-9619b4dd57394455874c733c1de58202
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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