Dimethylbarbituric acid → 3-Fluoro-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol

HRID 2113892Notes

Reaction equation

HRID 2113892 reaction equation
CN1C(=O)CC(=O)N(C)C1=O.C([O:15][C:16]1[CH:30]=[CH:29][C:19]([CH2:20][O:21][CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[N:25]2)=[C:18]([F:31])[CH:17]=1)C=C>ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:31][C:18]1[CH:17]=[C:16]([OH:15])[CH:30]=[CH:29][C:19]=1[CH2:20][O:21][CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[N:25]1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 692938261-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazole

Product 1

HCID 692922963-Fluoro-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenolYield 56.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 10.4 g (66.9 mmol) 1,3-dimethyl-pyrimidine-2,4,6-trione and 774 mg (0.67 mmol) tetrakis-(triphenylphosphine)-palladium in 100 ml dichloromethane was added dropwise a solution of 6.18 g (22.3 mmol) 1-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazole in 30 ml dichloromethane and stirring was continued for 24 hours at 40° C. It was allowed to cool down over night. The reaction mixture was extracted with three 100 ml portions of sodium bicarbonate solution, the organic extract was dried, evaporated and purified by chromatography on silica (ethyl acetate/dichloromethane 3:7) to yield 2.97 g (56%) 3-fluoro-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol as oil.

Workup

  1. temperatureto cool down over night
  2. extractionThe reaction mixture was extracted with three 100 ml portions of sodium bicarbonate solution
  3. extractionthe organic extract
  4. customwas dried
  5. customevaporated
  6. custompurified by chromatography on silica (ethyl acetate/dichloromethane 3:7)

Sources & evidence

ORD record
ord-71c5c50c286544e6a539afd2717bd5fe
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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