Diisopropylethylamine → 2-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

HRID 1864039Notes

Reaction equation

HRID 1864039 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:22]=[CH:21][CH:20]=[CH:19][C:12]=1[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[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:22]=[CH:21][CH:20]=[CH:19][C:12]=2[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 944112-Amino-N-isopropylbenzamideHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 579742032-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask was charged with 2,4,5-trichloropyrimidine (2.0 g, 6.8 mmol), 2-amino-N-(1-methylethyl)benzamide (1.2 g, 7.1 mmol), di-isopropyl-ethylamine (1.4 mL, 8.1 mmol) and 30 mL 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 diethyl ether to afford 2-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (2.0 g, 90%)

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 diethyl ether

Sources & evidence

ORD record
ord-1b353855387149e09019e5c09b6d4fbe
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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