Water → 2-[2-(N-monomethylamino)pyrimidine-4-yl]-6-(2-fluoroethoxy)benzothiophene

HRID 454813Notes

Reaction equation

HRID 454813 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.CO.[CH3:23][NH2:24].O>O1CCCC1>[CH3:23][NH:24][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 57454252Monomethylamine methanolHCID 866465562-(2-Chloropyrimidine-4-yl)-6-(2-fluoroethoxy)benzothiophene

Product 1

HCID 469477252-[2-(N-monomethylamino)pyrimidine-4-yl]-6-(2-fluoroethoxy)benzothiopheneYield 63.4%

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 2.0 M methylamine methanol solution (NH2Me in MeOH, 0.26 mL, 0.52 mmol) was added to the reaction mixture and stirred at room temperature for 3 days. 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-(N-monomethylamino)pyrimidine-4-yl]-6-(2-fluoroethoxy)benzothiophene (1-35, 50 mg, 63%) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-974480f09ca94602a4844db088e84a84
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

Loading…