Ammonium Chloride → 5-bromo-N-[4-(trifluoromethyl)pyrimidin-2-yl]benzene-1,3-diamine

HRID 595148Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][N:13]=2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[NH4+].[Cl-]>C(O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([NH:11][C:12]2[N:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][N:13]=2)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-(3-Bromo-5-nitrophenyl)-4-(trifluoromethyl)pyrimidin-2-amine (4.76 g, 13.11 mmol) was dissolved in ethanol (131 ml) and saturated solution of NH4Cl (1 mL) was added followed by Fe (3.66 g, 65.5 mmol). The reaction mixture was stirred at 80° C. for 30 minutes then cooled to room temperature. The solution was filtered through a short pad of silica gel and eluted with EtOAc. The phase were separated, the organics were dried, filtered, concentrated under reduced pressure to afford 5-bromo-N-[4-(trifluoromethyl)pyrimidin-2-yl]benzene-1,3-diamine as a beige powder.

Workup

temperaturethen cooled to room temperature
filtrationThe solution was filtered through a short pad of silica gel
washeluted with EtOAc
customThe phase were separated
customthe organics were dried
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ace4d398f5d9464ba65fd1e3f06cf8c1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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