Chloroform → N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine

HRID 1926588Notes

Reaction equation

HRID 1926588 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:17][C:18]1[C:23]([NH2:24])=[CH:22][C:21]([N+:25]([O-:27])=[O:26])=[CH:20][N:19]=1.[H-].[Na+].C(Cl)(Cl)Cl>CN(C=O)C.O>[N+:25]([C:21]1[CH:22]=[C:23]([NH:24][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:8]=[CH:7][N:6]=2)[C:18]([CH3:17])=[N:19][CH:20]=1)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 24758Sodium hydrideHCID 469097742-Methyl-5-nitropyridin-3-amineHCID 469098552-(Methylsulfonyl)-4-(pyridin-3-yl)pyrimidine

Product 1

HCID 46910559N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-methylsulfonyl-4-(pyridin-3-yl)pyrimidine (3.0 g) and 2-methyl-3-amino-5-nitropyridine (5.0 g) in DMF (50 mL) at 0-5° C. was added sodium hydride (60%, 2.3 g). The reaction mixture was naturally warmed to room temperature and stirred for 6 hours. Chloroform (50 mL) and water (50 mL) were added to the reaction and the phases were separated, the aqueous phase was extracted with Chloroform (2×100 mL). The organic extracts were combined, dried, filtered, concentrated and the residue was purified by chromatography to provide_N-(5-nitro-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (5.2 g).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with Chloroform (2×100 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography to provide_N-(5-nitro-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (5.2 g)

Sources & evidence

ORD record
ord-c1dae2c21b0740288ff7a3fedcf5757c
Source dataset
uspto-grants-2012_05
Patent number
US08183242B2

Reaction notes

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