Sodium hydride → HCID 57975861, compound

HRID 2388988Notes

Reaction equation

HRID 2388988 reaction equation
CC(N(C)C)=O.Cl[C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[H-].[Na+].[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([F:24])[CH:18]=1>O>[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:19]([F:24])[CH:18]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 744042-ChloropyrimidineHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 57975861HCID 57975861, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylacetamide (10 ml) was added slowly to a mixture of 2-chloropyrimidine (1 g, 8.7 mmol), sodium hydride (0.8 g, 34.9 mmol), and 4-bromo-2-fluoro-aniline (1.6 g, 8.7 mmol) and the resulting mixture was stirred overnight at room temperature. Water was added slowly and the resulting mixture extracted three times with ethyl acetate. The organic phase bas washed with brine, dried over sodium sulfate and concentrated to dryness. Flash chromatography on silica gel chromatography using a gradient of ethyl acetate and hexane afforded (4-bromo-2-fluoro-phenyl)-pyrimidin-2-yl-amine (1.3 g, 56% yield). 1H NMR (500 MHz, DMSO-d6) δ 6.85 (m, 1H), 7.37 (d, 1H), 7.55 (d, 1H), 7.74 (m, 1H), 8.44 (s, 2H), 9.21 (s, 1H). MS: m/z 269.0 (M+H+).

Workup

  1. extractionthe resulting mixture extracted three times with ethyl acetate
  2. washThe organic phase bas washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4e222011d38f42218ec74209cc0c44dd
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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