1-Bromooctane → 5-(2,3-Difluoro-4-octyloxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine

HRID 376767Notes

Reaction equation

HRID 376767 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:21]=2)=[N:14][CH:15]=1.Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:21]=2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 81401-BromooctaneHCID 193591085-(2,3-Difluoro-4-hydroxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine

Product 1

HCID 110383765-(2,3-Difluoro-4-octyloxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The etherification of 12 mmol of 5-(2,3-difluoro-4-hydroxyphenyl)-2-(6-hexyloxypyridin-3-yl)pyrimidine using 13.2 mmol of 1-bromooctane in 100 ml of DMF is carried out analogously to the procedure indicated for Example 3. The crude product is chromatographed on silica gel 60 using dichloromethane as eluent and is recrystallized from n-heptane and toluene, giving 3.6 g (61%) of colorless crystals, whose analytical data correspond to those of the compound obtained as described in 1a).

Workup

  1. customThe crude product is chromatographed on silica gel 60 using dichloromethane as eluent
  2. customis recrystallized from n-heptane and toluene

Sources & evidence

ORD record
ord-3029bf716e1d49bd8a81cf4613091e41
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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