Water → 2-(2-Methoxypyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiophene

HRID 454812Notes

Reaction equation

HRID 454812 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH2:19][F:20])[CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:21][OH:22].C[O-].[Na+].O>O1CCCC1>[CH3:21][O:22][C:2]1[N:7]=[C:6]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH2:19][F:20])[CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23694274Sodium methanolate methanolHCID 866465562-(2-Chloropyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiophene

Product 1

HCID 469475492-(2-Methoxypyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiopheneYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Chloropyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiophene (105b, 80 mg, 0.26 mmol) obtained in Preparation Example 20 was dissolved in anhydrous tetrahydrofuran (4 mL). A 0.5 M sodium methoxide methanol solution (NaOMe in MeOH, 1.0 mL, 0.5 mmol) was added to the reaction mixture and stirred at room temperature for 18 hours. To the reaction mixture was added water, and organic compounds were extracted with ethyl acetate and evaporated after a treatment with sodium sulfate. Column chromatography was performed to give the target compound 2-(2-methoxypyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiophene (1-34, 60 mg, 70%) as a yellow solid.

Workup

  1. extractionwere extracted with ethyl acetate
  2. customevaporated after a treatment with sodium sulfate

Sources & evidence

ORD record
ord-f475f210ea684d1ba8a3c1ee54f2b3ca
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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