Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → Cyclopentyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine

HRID 459952Notes

Reaction equation

HRID 459952 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[NH2:13].[CH:14]1([NH:19][C:20]2[C:25]([CH:26]=O)=[CH:24][N:23]=[C:22]([S:28][CH3:29])[N:21]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[CH:14]1([NH:19][C:20]2[C:25]([CH:26]=[N:13][C:3]3[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=3[F:12])=[CH:24][N:23]=[C:22]([S:28][CH3:29])[N:21]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineHCID 107998964-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 18444836Cyclopentyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a 1-L round bottom flask, 10.00 g (0.0528 mol) of 2,6-difluoro-3,5-dimethoxy-phenylamine and 12.42 g (0.0523 mol) of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde in 500 mL of toluene with 3.65 g (0.0157 mol) of camphorsulfonic acid was fitted with a Dean Stark trap and heated at reflux. During the day, the toluene was drained three times from the finger and continued heating at reflux under nitrogen atmosphere overnight. The toluene was concentrated in vacuo and dried to give 25.30 g (quantitative) of the title compound. No further purification was necessary. MS (APCI) (m+1)/z 409.2.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperaturecontinued heating
  4. temperatureat reflux under nitrogen atmosphere overnight
  5. concentrationThe toluene was concentrated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-2eeebb61abd64651bda7230d69a15e8d
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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