Cyclopentanol → 5-Bromo-2-cyclopentyloxypyrimidine

HRID 76131Notes

Reaction equation

HRID 76131 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:9]=[N:10][C:11](Cl)=[N:12][CH:13]=1.[H-].[Na+]>O1CCOCC1>[Br:7][C:8]1[CH:9]=[N:10][C:11]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 497587165-Bromo-2-cyclopentyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

36.3 μL (0.40 mmol) cyclopentanol and 38.7 mg (0.20 mmol) 5-bromo-2-chloro-pyrimidine are added to 1.5 mL dioxane and cooled down to 0° C. Then the reaction mixture is charged with 24.0 mg NaH. After removing of the cooling bath the reaction mixture is stirred at r.t. over night. The reaction is quenched by the addition of water. The solvent is removed under vacuo and the residue is dissolved in DCM, washed with water and dried with MgSO4. The solvent is removed under reduced pressure. The crude product is used without further purification.

Workup

  1. customAfter removing of the cooling bath the reaction mixture
  2. customThe reaction is quenched by the addition of water
  3. customThe solvent is removed under vacuo
  4. dissolutionthe residue is dissolved in DCM
  5. washwashed with water
  6. dry with materialdried with MgSO4
  7. customThe solvent is removed under reduced pressure
  8. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-0bd4fd29ba444a658ad3a4158e44f646
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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