2'-Aminoacetophenone → HCID 57632401, compound

HRID 2108684Notes

Reaction equation

HRID 2108684 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[O:19])[CH3:18].C(=O)(O)[O-].[Na+]>CCO.C1COCC1>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17](=[O:19])[CH3:18])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 110862'-AminoacetophenoneHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 57632401HCID 57632401, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2,4-dichloropyrimidine (1.25 g, 5.5 mmol) and 1-(2-aminophenyl)ethanone (675 mg, 5.0 mmol) with sodium bicarbonate (1.26 g, 15.0 mmol) in 4:1 EtOH/THF (7.5 mL) was stirred at 80° C. for 14 hours. The reaction was cooled to room temperature and the resulting mixture was filtered, washing the solid with cold EtOH. The collected solid was stirred in hot water, filtered, and the resulting solid washed with cold EtOH. The solid was then dried under vacuum to give 1-{2-[(5-bromo-2-chloropyrimidin-4-yl)amino]phenyl}ethanone (761 mg, 47%) as a yellow solid. 1H NMR (DMSO-d6): δ 11.91 (s, 1H), 8.60-8.64 (m, 2H), 8.15 (d, 1 H), 7.74 (t, 1 H), 7.31 (t, 1 H), 2.72 (s, 3 H). MS m/z 326 (M+1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe resulting mixture was filtered
  3. washwashing the solid with cold EtOH
  4. stirringThe collected solid was stirred in hot water
  5. filtrationfiltered
  6. washthe resulting solid washed with cold EtOH
  7. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-391078dea7c84a61ba9eef7a4614485d
Source dataset
uspto-grants-2009_04
Patent number
US07514446B2

Reaction notes

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