4,6-Dichloropyrimidine → n2-(6-Chloropyrimidin-4-yl)-n6-methylpyridine-2,6,diamine

HRID 2093502Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[N:4]=1.Cl[C:11]1[CH:16]=[C:15]([Cl:17])[N:14]=[CH:13][N:12]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([NH:2][CH3:1])[N:4]=2)[CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-methylamino-6-aminopyridine (0.5 g, 4.04 mmol), 4,6-dichloropyrimidine (1.51 g, 10.13 mmol), DIPEA (1.5 g, 12.17 mmol) in n-butanol (5 mL) was heated at 120° C. for 16 h. The reaction mixture was cooled, was concentrated under reduced pressure and the residue was taken in dichloromethane (25 mL). The dichloromethane solution was washed with NaHCO3 solution (2 mL), water (2 mL) and brine (2 mL), was dried over Na2SO4 and was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 60-120, petroleum ether/ethyl acetate, 6/4) to give N2-(6-chloropyrimidin-4-yl)-N6-methylpyridine-2,6,diamine (0.3 g, 33%) as a yellow solid.

Workup

temperatureThe reaction mixture was cooled
concentrationwas concentrated under reduced pressure
washThe dichloromethane solution was washed with NaHCO3 solution (2 mL), water (2 mL) and brine (2 mL)
dry with materialwas dried over Na2SO4
concentrationwas concentrated under reduced pressure
customThe residue was purified by column chromatography (SiO2, 60-120, petroleum ether/ethyl acetate, 6/4)

Sources & evidence

ORD record: ord-4396c12b45a64a86b4150fada66605f1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445498B2

Reaction notes

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