Sodium hydride → HCID 118307774, compound

HRID 718362Notes

Reaction equation

HRID 718362 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:14]1[N:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1>C1COCC1>[Br:20][C:17]1[CH:16]=[N:15][C:14]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 820684-Fluorophenethyl AlcoholHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 118307774HCID 118307774, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-fluorophenyl)ethanol (0.566 g) in THF (10 mL) was added NaH (0.269 g). The mixture was stirred at room temperature for 2 hours, before 2,5-dibromopyrimidine (0.8 g) was added. The mixture was stirred at room temperature for 16 h. The reaction was quenched with water and extracted with EtOAc (2×20 mL). The organic layers were combined, dried over MgSO4 and concentrated under vacuum. The residue was purified by silica gel column (Hex/EtOAc=100:5) to give 5-bromo-2-(4-fluorophenethoxy)pyrimidine (0.7 g). LCMS (M+H)=297.0.

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel column (Hex/EtOAc=100:5)

Sources & evidence

ORD record
ord-43c4573adbed43d9b37c13e25b9e792d
Source dataset
uspto-grants-2015_11
Patent number
US09193720B2

Reaction notes

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