Water → N-(5-bromo-2-nitrophenyl)-2-chloropyrimidin-4-amine

HRID 1398501Notes

Reaction equation

HRID 1398501 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14](F)[CH:13]=1.O>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[C:16]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3457522-Chloro-4-aminopyrimidineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 86669571N-(5-bromo-2-nitrophenyl)-2-chloropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-chloropyrimidin-4-amine (8.83 g, 68.18 mmol) in THF (250 mL) at 0° C. was added sodium hydride (60% dispersion in oil, 4.36 g, 181.82 mmol) portionwise. The reaction mixture was stirred at 0° C. to RT for 10 minutes before addition of 4-bromo-2-fluoro-1-nitrobenzene (10 g, 45.45 mmol). The reaction mixture was stirred at 65° C. for 1 hr, then after cooling to RT, water was added resulting in formation of a yellow precipitate. The solid was collected by suction filtration and was washed with water. The filtrate was extracted with DCM. The organics were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Isolute column, 1% MeOH in DCM) then combined with the solid collected by suction filtration to give the title compound: 1HNMR (250 MHz, DMSO) δ 6.91 (1H, d, J=5.79 Hz), 7.61 (1H, dd, J=8.76, 2.21 Hz), 7.91-8.05 (2H, m), 8.29 (1H, d, J=5.79 Hz), 10.40 (1H, s); LC-MS: m/z=+328.9, 330.8 (M+H)+.

Workup

  1. temperatureafter cooling to RT
  2. customresulting in formation of a yellow precipitate
  3. filtrationThe solid was collected by suction filtration
  4. washwas washed with water
  5. extractionThe filtrate was extracted with DCM
  6. washThe organics were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (Isolute column, 1% MeOH in DCM)
  11. filtrationcollected by suction filtration

Sources & evidence

ORD record
ord-a704d7b7363d4e0493f102d19bc29062
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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