Ethylenediamine → HCID 12017518, compound

HRID 2303303Notes

Reaction equation

HRID 2303303 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].N1(O[C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:18]([C:29]([NH2:31])=[O:30])=[CH:17][N:16]=2)C2C=CC=CC=2N=N1.C(#N)C>O>[NH2:3][CH2:2][CH2:1][NH:4][C:15]1[N:20]=[C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:18]([C:29]([NH2:31])=[O:30])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6342AcetonitrileHCID 12017517HCID 12017517, compound

Product 1

HCID 12017518HCID 12017518, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3.0 ml portion of ethylenediamine was added to a mixture of 1.0 g of 2-(benzotriazol-1-yloxy)-4-(4-methylanilino)pyrimidine-5-carboxamide and 30 ml of acetonitrile, followed by stirring at room temperature for 1 hour and 40 minutes. Water was added to the reaction mixture, followed by extraction with a chloroform-isopropanol mixed solution. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure and then the thus obtained residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanol:aqueous ammonia) . By recrystallizing the thus obtained colorless solid from an ethyl acetate-ethanol mixed solvent, 471 mg of 2-(2-aminoethylamino)-4-(4-methylanilino)pyrimidine-5-carboxamide was obtained (colorless crystals).

Workup

  1. extractionfollowed by extraction with a chloroform-isopropanol mixed solution
  2. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customthe thus obtained residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanol:aqueous ammonia)
  5. customBy recrystallizing the thus obtained colorless solid from an ethyl acetate-ethanol mixed solvent

Sources & evidence

ORD record
ord-f50b98aa2401497a86ef34b61f7abe0d
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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