2-Pyridinemethanamine → 4-[4-(Methylsulfonyl)phenyl]-N-(pyridin-2-ylmethyl)-6-(trifluoromethyl)pyrimidin-2-amine

HRID 1836988Notes

Reaction equation

HRID 1836988 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)(=O)=O.[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>CC#N>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=[C:5]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[N:10]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 102231534-[4-(Methylsulfonyl)phenyl]-N-(pyridin-2-ylmethyl)-6-(trifluoromethyl)pyrimidin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.10 g, 0.26 mmol) in MeCN (4 ml) was added 2-(aminomethyl)-pyridine (0.14, 5 eq) and the resultant solution heated under reflux for 3 h. The cooled reaction mixture was concentrated in vacuo and purified by SPE chromatography using chloroform, diethyl ether, ethyl acetate, acetone and methanol as the eluotropic series of solvents. Concentration in vacuo of the combined fractions containing pure product gave the title compound as a colourless solid (0.086 g, 80%).

Workup

  1. temperatureunder reflux for 3 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by SPE chromatography
  5. concentrationConcentration in vacuo of the combined fractions
  6. additioncontaining pure product

Sources & evidence

ORD record
ord-aef2424bcef946ada83aa023afe11928
Source dataset
uspto-grants-2004_08
Patent number
US06780870B2

Reaction notes

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