Tetrahydrofuran → HCID 86646558, compound

HRID 454818Notes

Reaction equation

HRID 454818 reaction equation
[F:1][CH2:2][CH2:3][OH:4].O1CCCC1.[H-].[Na+].[Cl:12][C:13]1[N:18]=[CH:17][CH:16]=[C:15](Cl)[N:14]=1>O>[Cl:12][C:13]1[N:18]=[C:17]([O:4][CH2:3][CH2:2][F:1])[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 86646558HCID 86646558, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Fluoroethanol (0.30 mL, 4.95 mmol) was added to an anhydrous tetrahydrofuran (5 mL) solution containing sodium hydride (60% NaH, 200 mg, 4.95 mmol), and an anhydrous tetrahydrofuran (5 mL) solution having 2,4-dichloropyrimidine (104, 500 mg, 3.30 mmol) dissolved therein was slowly added. The reaction mixture was stirred for 30 minutes and water was added. Organic compounds were extracted with ethyl acetate. Then, the recovered organic solution was washed with an aqueous solution of saturated sodium chloride and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give 2-chloro-4-(2-fluoroethoxy)pyrimidine (106a, 237 mg, 41%) as a white solid.

Workup

  1. dissolutiondissolved
  2. additiontherein was slowly added
  3. extractionOrganic compounds were extracted with ethyl acetate
  4. washThen, the recovered organic solution was washed with an aqueous solution of saturated sodium chloride
  5. customevaporated after a treatment with sodium sulfate
  6. customPurification

Sources & evidence

ORD record
ord-0c4ef51cd9434ce6a9b28f7bf5125636
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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