Tetrahydrofuran → HCID 63867842, compound

HRID 2171673Notes

Reaction equation

HRID 2171673 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.C1COCC1.[H-].[Na+].[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1>CCOC(C)=O.O>[Br:15][C:16]1[CH:17]=[N:18][C:19]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 63867842HCID 63867842, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrahydro-2H-pyran-4-ol (200 mg) was mixed with THF (5 ml), and sodium hydride (55% suspended in oil) (120 mg) was added thereto, followed by stirring at room temperature for 5 minutes. 5-Bromo-2-chloropyrimidine (460 mg) was added to the reaction mixture, followed by stirring at room temperature. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 5-bromo-2-(tetrahydro-2H-pyran-4-yloxy)pyrimidine (361 mg).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-8636ff26fa874297ab94f43b2c56585a
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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