2-Methoxyethanol → 2-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

HRID 1362863

Reaction equation

HRID 1362863 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[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.COCCO>O>[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]([CH3:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 81531DiisopropylethylamineHCID 944112-Amino-N-isopropylbenzamide

Product 1

HCID 579742052-[(2-Chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamideYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A vessel was charged with 2,4-dichloro-5-methylpyrimidine (5.0 g, 28 mmol), 2-amino-N-(1-methylethyl)benzamide (5.46 g, 34.3 mmol), di-isopropyl-ethylamine (7.0 mL, 42 mmol) and 2-(methyloxy)ethanol (30 mL) and sealed and heated with stirring at 130° C. for 36 hours. The reaction was cooled to room temperature and 50 mL water was added dropwise to afford a milky white solution, which was heated to 100° C. to induce precipitation. The solution was cooled and the solid collected by filtration. The collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL). After drying, a white solid was collected (6.56 g, 77% yield) and identified as 2-[(2-chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, s) 8.56-8.63 (2H, m) 8.15 (1H, s) 7.81 (1H, dd, J=7.83, 1.52 Hz) 7.58 (1H, dd, J=15.66, 1.52 Hz) 7.17 (1H, dd, J=15.28, 1.14 Hz) 4.13 (1H, dd, J=14.02, 6.69 Hz) 2.18 (3H, s) 1.18 (6H, d, J=6.57 Hz).

Workup

  1. customsealed
  2. temperatureheated
  3. temperatureThe reaction was cooled to room temperature
  4. customto afford a milky white solution, which
  5. temperaturewas heated to 100° C.
  6. customprecipitation
  7. temperatureThe solution was cooled
  8. filtrationthe solid collected by filtration
  9. washThe collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL)
  10. customAfter drying
  11. customa white solid was collected (6.56 g, 77% yield)

Sources & evidence

ORD record
ord-5c32994a90f94adaa0a3c9ffe1861427
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Linked notes

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