Sodium hydride → 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide

HRID 449902

Reaction equation

HRID 449902 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=2)[CH:5]=[C:4]([CH3:19])[N:3]=1.[H-].[Na+].[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25](Cl)=[O:26]>CN(C)C=O>[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:24]=1[C:25]([NH:15][C:13]1[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=[C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:19])[N:3]=[C:2]([CH3:1])[N:7]=2)[CH:14]=1)=[O:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 783922,6-Dichlorobenzoyl chlorideHCID 67128909N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine

Product 1

HCID 671286552,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, 1.337 mmol) in anhydrous N,N-dimethylformamide (10 mL) under nitrogen was added sodium hydride (0.064 g, 2.67 mmol, 60% dispersion in mineral oil) in one portion. The reaction mixture was stirred at 0° C. for 15 mins and then a solution of 2,6-dichlorobenzoyl chloride (220 uL, 1.5 mmol) in DMF (1.5 mL) was added dropwise. The mixture was stirred at room temperature for 3.5 hours and then quenched with water (60 mL). The mixture was extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (20-80% ethyl acetate/heptane) to give 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide (0.57 g, yield: 100%). LCMS (ESI) m/z: 433.1 [M+H+].

Workup

  1. stirringThe mixture was stirred at room temperature for 3.5 hours
  2. customquenched with water (60 mL)
  3. extractionThe mixture was extracted with ethyl acetate (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (20-80% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-f02c82635fe04150bb5d7bf051a18c31
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Linked notes

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