Potassium Carbonate → 5-n-Heptyl-2-[2,3-difluoro-4-(2-fluorooctyloxy)phenyl]pyrimidine

HRID 2253721Notes

Reaction equation

HRID 2253721 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:21])[C:15]=2[F:22])=[N:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C([O-])([O-])=O.[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:33][CH:34]([F:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])(=O)=O>C(C(C)=O)C>[CH2:1]([C:8]1[CH:13]=[N:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:33][CH:34]([F:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:16]([F:21])[C:15]=2[F:22])=[N:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14297706HCID 14297706, compoundHCID 1357870105-Heptyl-2-(2,3-difluoro-4-hydroxyphenyl)pyrimidine

Product 1

HCID 200874145-n-Heptyl-2-[2,3-difluoro-4-(2-fluorooctyloxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

0.08 mol of 5-heptyl-2-(2,3-difluoro-4-hydroxyphenyl)pyrimidine, together with 11.6 g of K2CO3 and 25.6 g of optically active 2-fluoro-1-octyl tosylate in 70 ml of methyl ethyl ketone, are refluxed for 12 hours under a protective gas atmosphere. The reaction mixture is then hydolysed [sic], and the product is then worked up in a customary manner and purified by chromatography, to give optically active 5-n-heptyl-2-[2,3-difluoro-4-(2-fluorooctyloxy)phenyl]pyrimidine of melting point 56° C.

Workup

  1. custompurified by chromatography

Sources & evidence

ORD record
ord-a22054eb94364785900dfe44544729b2
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

Loading…