2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine → 4-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine

HRID 2368191Notes

Reaction equation

HRID 2368191 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 866775212-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 866775204-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine (50 mg, 0.145 mmol) was added to the palladium/carbon (10 mg, 0.015 mmol) in ethanol (25 mL) and the applied hydrogen gas at 8 psi for 2 h at rt. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite; the solvent was removed by vacuum; and the crude material was purified by flash chromatography (2% CH3OH/DCM) to yield the title compound (35 mg, 0.145 mmol) as a solid. 1H NMR: (CDCl3, 400 MHz): δ 8.40 (s, 1H), 7.65 (m, 1H), 7.27-7.17 (m, 4H), 7.13-7.09 (m, 2H), 6.77 (m, 1H), 6.68 (m, 1H). ESI-MS: m/z 315.0 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was removed by vacuum
  4. customand the crude material was purified by flash chromatography (2% CH3OH/DCM)

Sources & evidence

ORD record
ord-3240004659ba43d7ba3f5536048d1727
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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