Water → 2-[2-(2-Fluoroethoxy)pyrimidine-4-yl]-6-methoxybenzothiophene

HRID 454810

Reaction equation

HRID 454810 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[C:8]1[N:13]=[C:12]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:17]=3[CH:18]=2)[CH:11]=[CH:10][N:9]=1.O>O1CCCC1>[F:1][CH2:2][CH2:3][O:4][C:8]1[N:13]=[C:12]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:17]=3[CH:18]=2)[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 866465552-(2-Chloropyrimidine-4-yl)-6-methoxybenzothiophene

Product 1

HCID 469475462-[2-(2-Fluoroethoxy)pyrimidine-4-yl]-6-methoxybenzothiopheneYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

2-Fluoroethanol (32 μL, 0.54 mmol) and sodium hydride (NaH, 22 mg, 0.54 mmol) were dissolved in a solvent of anhydrous tetrahydrofuran (4 mL) under nitrogen, and the mixture was added to a solution of anhydrous tetrahydrofuran (3 mL) containing 2-(2-chloropyrimidine-4-yl)-6-methoxybenzothiophene (105a, 100 mg, 0.36 mmol) obtained in Preparation Example 19 dissolved therein at room temperature, heated at 60° C. for 10 hours, cooled to room temperature, followed by adding water. 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-(2-fluoroethoxy)pyrimidine-4-yl]-6-methoxybenzothiophene (1-31, 79 mg, 72%) as a pale yellow solid.

Workup

  1. customobtained in Preparation Example 19
  2. dissolutiondissolved
  3. temperaturecooled to room temperature
  4. extractionOrganic compounds were extracted with ethyl acetate
  5. customevaporated after a treatment with sodium sulfate

Sources & evidence

ORD record
ord-064ca6722d164b2d83251a86eeb6972d
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Linked notes

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