4-Pyridinemethanamine → HCID 10272841, compound

HRID 1836986Notes

Reaction equation

HRID 1836986 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][N:30]=[CH:29][CH: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][N:30]=[CH:29][CH:28]=3)[N:10]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 111764432-(Methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine

Product 1

HCID 10272841HCID 10272841, compoundYield 57%

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 4-(aminomethyl)-pyridine (0.14 ml, 5 eq) and the resultant solution heated under reflux for 18 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 (0.061 g, 57%).

Workup

  1. temperatureunder reflux for 18 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-af54241f17ee407f939bd05cf54e55ac
Source dataset
uspto-grants-2004_08
Patent number
US06780870B2

Reaction notes

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