4,6-Dichloro-5-nitropyrimidine → 6-chloro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5-nitropyrimidin-4-amine hydrochloride

HRID 1925945Notes

Reaction equation

[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[NH2:16]>CN1CCCC1=O.C(OCC)(=O)C>[ClH:1].[Cl:11][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([O:20][C:21]3[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[C:13]([CH3:12])[CH:14]=2)[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: -15 °C

Procedure

4,6-Dichloro-5-nitropyrimidine (9.7 g) was dissolved in 1-methyl-2-pyrrolidone (25.7 mL), a solution of 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (5.35 g) in 1-methyl-2-pyrrolidone (10 mL) was added dropwise under cooling at −15° C., and the mixture was stirred at −10° C. to 0° C. for 1 hr. The mixture was diluted with ethyl acetate (100 mL) and stirred at 0° C. for 15 min. The precipitated crystals were collected by filtration, washed with ethyl acetate (30 mL), and dried under reduced pressure to give the title compound (7.34 g).

Workup

stirringstirred at 0° C. for 15 min
filtrationThe precipitated crystals were collected by filtration
washwashed with ethyl acetate (30 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-eb136e485f9a42d68d6d62686c84a193
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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