Diisopropylethylamine → 2-[(2,5-dichloropyrimidin-4-yl)amino]-N,N-dimethylbenzamide

HRID 1362856Notes

Reaction equation

HRID 1362856 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([N:15]([CH3:17])[CH3:16])=[O:14].C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 47781752-Amino-N,N-dimethylbenzamide

Product 1

HCID 579741612-[(2,5-dichloropyrimidin-4-yl)amino]-N,N-dimethylbenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask was charged with 2,4,5-trichloropyrimidine (1.0 g, 3.4 mmol), 2-amino-N,N-dimethylbenzamide (587 mg, 3.5 mmol), di-isopropyl-ethylamine (712 μL, 4.08 mmol) and 15 mL of isopropanol. The flask was fitted with a reflux condenser and the reaction was heated to reflux and stirred for 18 h. A white solid appeared in the reaction mixture. The reaction was cooled to 0° C. and filtered and solid was washed with ether to afford 2-[(2,5-dichloro-4-pyrimidinyl)amino]-N,N-dimethylbenzamide (896 mg, 94%):

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperaturethe reaction was heated
  3. temperatureto reflux
  4. filtrationfiltered
  5. washsolid was washed with ether

Sources & evidence

ORD record
ord-0c0cb71266ad4b488b58967c399f7b4f
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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