Pyridine → HCID 21833461, compound

HRID 1740858Notes

Reaction equation

HRID 1740858 reaction equation
[NH2:1][C:2]1[C:3]([NH:14][CH2:15][C:16]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:26]([NH:1][C:2]1[C:3]([NH:14][CH2:15][C:16]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21833522HCID 21833522, compound

Product 1

HCID 21833461HCID 21833461, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(5-amino-2-phenyl-4-pyrimidinylamino)-N-methyl-N-phenylacetamide (3.6 g) obtained in Example 124, acetic anhydride (10 ml) and pyridine (7 ml) is stirred at room temperature for four hours. To the reaction mixture is added chloroform, and the mixture is washed with 1N hydrochloric acid, then washed with a saturated aqueous sodium hydrogen carbonate solution. The chloroform layer is collected, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from ethanol to give the desired compound (4.0 g), m.p. 200-201° C.

Workup

  1. washthe mixture is washed with 1N hydrochloric acid
  2. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  3. customThe chloroform layer is collected
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e420207dd1cc4f0e915c7bac31dd80f2
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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