6-chloro-2-(5-nitropyridin-2-yl)-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine → 2-(5-aminopyridin-2-yl)-6-chloro-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine

HRID 2112613Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[N:5]=[C:4]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:3]=1[C:23]1[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=1[F:31]>CO.C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:3]([C:23]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=3[F:31])=[C:2]([Cl:1])[N:7]=2)=[N:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-2-(5-nitropyridin-2-yl)-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine (101 mg, 0.22 mmol) and Iron powder (256 mg, 4.58 mmol) in 2 mL of methyl alcohol and 1 mL of acetic acid is heated at 100° C. for 1 h. The reaction mixture is cooled to room temperature and diluted with ethyl acetate. The organic layer is washed with saturated sodium bicarbonate and then with saturated sodium chloride, dried over magnesium sulfate, filtered, concentrated and dried under reduced pressure to yield 2-(5-aminopyridin-2-yl)-6-chloro-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine as a light yellow oil (100 mg). MS: m/z 434.2 (M+H). This product is used in the next step with out further purification.

Workup

temperatureThe reaction mixture is cooled to room temperature
washThe organic layer is washed with saturated sodium bicarbonate
dry with materialwith saturated sodium chloride, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customdried under reduced pressure

Sources & evidence

ORD record: ord-f59a10faecf14a2f87f0ffae601de550
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524849B2

Reaction notes

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