4-(Aminomethyl)cyclohexanecarboxylic acid → 4-[(4,5-Diphenylpyrimidin-2-ylamino)methyl]cyclohexanecarboxylic acid

HRID 2235001Notes

Reaction equation

HRID 2235001 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1.Cl[C:19]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:21][N:20]=1>C1(C)C=CC=CC=1>[C:25]1([C:23]2[C:22]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:21][N:20]=[C:19]([NH:7][CH2:8][CH:9]3[CH2:10][CH2:11][CH:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]3)[N:24]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 55264-(Aminomethyl)cyclohexanecarboxylic acidHCID 10796Cesium carbonateHCID 126742762-Chloro-4,5-diphenylpyrimidine

Product 1

HCID 236526954-[(4,5-Diphenylpyrimidin-2-ylamino)methyl]cyclohexanecarboxylic acidYield 62.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

550 mg (1.69 mmol) of cesium carbonate were added to a suspension of 133 mg (0.84 mmol) of 4-aminomethylcyclohexanecarboxylic acid in 5 ml of toluene, and the mixture was stirred at room temperature. After 30 minutes, 150 mg (0.56 mmol) of 2-chloro-4,5-diphenyl-pyrimidine were added, and the mixture was stirred at 120° C. for 31 hours. The solvent was removed in vacuo and the residue was mixed with dichloromethane and water. The resulting precipitate was filtered off with suction. 135 mg (62%) of the desired product were obtained.

Workup

  1. stirringthe mixture was stirred at 120° C. for 31 hours
  2. customThe solvent was removed in vacuo
  3. additionthe residue was mixed with dichloromethane and water
  4. filtrationThe resulting precipitate was filtered off with suction

Sources & evidence

ORD record
ord-2c2c878a42fe493b989ccf7d23c40323
Source dataset
uspto-grants-2010_05
Patent number
US07713988B2

Reaction notes

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