Triethylamine → N-(5-(4-chloromethylbenzoylamino)-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine

HRID 736303Notes

Reaction equation

HRID 736303 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(N(CC)CC)C.[Cl:29][CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>O1CCCC1>[Cl:29][CH2:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([NH:9][C:10]3[N:15]=[C:14]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:13]=[CH:12][N:11]=3)[CH:3]=2)=[O:36])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

Product 1

HCID 68817335N-(5-(4-chloromethylbenzoylamino)-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amineYield 114.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3-amino-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (11 g, 39.8 mmol) was dissolved in tetrahydrofuran (100 ml), triethylamine (8.3 ml, 59.5 mmol) was added thereto, and the mixture was stirred for 30 minutes. 4-Chloromethyl benzoyl chloride (2.03 g, 10.78 mmol) was added, and the resulting mixture was reacted under reflux for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated and crystallized from methylene chloride to give N-(5-(4-chloromethylbenzoylamino)-4-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine (5.3 g).

Workup

  1. customthe resulting mixture was reacted
  2. temperatureunder reflux for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customcrystallized from methylene chloride

Sources & evidence

ORD record
ord-1fd4856e151f48e9bfd28a4c84aacd0b
Source dataset
uspto-grants-2009_09
Patent number
US07595323B2

Reaction notes

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