1-Bromooctane → HCID 19359105, compound

HRID 376768Notes

Reaction equation

HRID 376768 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][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=2)=[N:14][CH:15]=1.Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[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][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 81401-BromooctaneHCID 19359092HCID 19359092, compound

Product 1

HCID 19359105HCID 19359105, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The etherification of 1.3 mmol of 5-(2,3-difluoro-4-hydroxyphenyl)-2-(6-dodecyloxypyridin-3-yl)pyrimidine using 1.7 mmol of 1-bromooctane in 80 ml of DMF is carried out analogously to the procedure indicated for Example 3. Chromatographic purification on silica gel 60 using dichloromethane as eluent and recrystallization from methanol gives 380 mg (51%) of colorless crystals, X 67 X1 76 SC 118-123 SA 147 I.

Workup

  1. customChromatographic purification on silica gel 60 using dichloromethane as eluent
  2. customrecrystallization from methanol

Sources & evidence

ORD record
ord-d57177ec45f84e29a24694436653196c
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

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