Pyridine → 4-Pyrrolidinopyridine

HRID 378191Notes

Reaction equation

HRID 378191 reaction equation
C(C1[CH:16]=[CH:15][C:14]([C:17]2[N:22]=[CH:21][C:20](O)=[CH:19][N:18]=2)=CC=1)=CCCCCCCCC.N1C=CC=[CH:26][CH:25]=1>ClCCl>[N:22]1([C:21]2[CH:20]=[CH:19][N:18]=[CH:26][CH:25]=2)[CH2:16][CH2:15][CH2:14][CH2:17]1

Participants

4

Reactant 2

HCID 1049PyridineHCID 540193422-{4-(1-Decenyl)-phenyl}-5-hydroxypyrimidine

Product 1

HCID 755674-Pyrrolidinopyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reactor was charged with 1.0g (2.67 mmol) of the 2-{4-(1-decenyl)-phenyl}-5-hydroxypyrimidine obtained above, 2 ml of pyridine, 0.01 g of 4-pyrrolidinopyridine and 20 ml of dichloromethane. While cooling the mixture to a temperature not higher than 0° C. in an atmosphere of nitrogen gas, 1.13 g (4 mmol) of trifluoromethanesulfonic acid anhydride was dropwise added and stirred for two hours. After extraction with water, the organic layer was washed successively with 1 N-hydrochloric acid and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, purification of the residue by silica gel column chromatography gave 1.06 g (yield 90%) of 2-{4-(1-decenyl)-phenyl}-5-trifluoromethylsulfonyloxypyrimidine.

Sources & evidence

ORD record
ord-ffc72542f9eb4e7db5f3183304c82627
Source dataset
uspto-grants-2000_02
Patent number
US06030546

Reaction notes

Loading…