Pyridine → 4-Pyrrolidinopyridine

HRID 725685Notes

Reaction equation

HRID 725685 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 1.0 g (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 1N-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-0404edb3356942dab7078a617ea93ab7
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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