Acetyl chloride → 2-[(2-Acetylaminoethyl)amino]-4-(3-methylanilino)pyrimidine-5-carboxamide

HRID 2303308Notes

Reaction equation

HRID 2303308 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][N:17]=1.C(OCC)(=O)C>C1COCC1.O>[C:1]([NH:12][CH2:13][CH2:14][NH:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=2)[C:19]([C:30]([NH2:32])=[O:31])=[CH:18][N:17]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 98173492-(2-Aminoethylamino)-4-(m-tolylamino)pyrimidine-5-carboxamide

Product 1

HCID 184608402-[(2-Acetylaminoethyl)amino]-4-(3-methylanilino)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An 87 μl portion of acetyl chloride and −170 μl of triethylamine were added to a mixture of 318 mg of 2-(2-aminoethylamino)-4-(3-methylanilino)pyrimidine-5-carboxamide and 20 ml of ethyl acetate, followed by stirring at room temperature for 30 minutes. Water and THF were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from a mixed solvent of THF and ethyl acetate, thereby obtaining 198 mg of 2-[(2-acetylaminoethyl)amino]-4-(3-methylanilino)pyrimidine-5-carboxamide (colorless crystals).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was recrystallized from a mixed solvent of THF and ethyl acetate

Sources & evidence

ORD record
ord-9c5a6a758bab411dbbcf3ad802ae517c
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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