Sodium hydride → 5-Bromo-2-cyclobutoxypyrimidine

HRID 467462Notes

Reaction equation

HRID 467462 reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:8]=[N:9][C:10](Cl)=[N:11][CH:12]=1.[H-].[Na+]>O1CCOCC1>[Br:6][C:7]1[CH:8]=[N:9][C:10]([O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 497587045-Bromo-2-cyclobutoxypyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2.42 mL (31.0 mmol) cyclobutanol and 3.00 g (15.5 mmol) 5-bromo-2-chloro-pyrimidine are added to 40 mL dioxane and cooled down to 0° C. Then the reaction mixture is charged with 1.86 g (46.5 mmol) NaH. After removing of the cooling bath the reaction mixture is stirred at r.t. for 1 h. The reaction is quenched by the addition of water and sat. aq. NaHCO3 solution. The dioxane is removed in vacuo and the aq. residue is extracted with DCM. The org. phases are combined, washed with water, dried with MgSO4 and filtered. 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 and sat. aq. NaHCO3 solution
  3. customThe dioxane is removed in vacuo
  4. extractionthe aq. residue is extracted with DCM
  5. washwashed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent is removed under reduced pressure
  9. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-d657cd38409a4d04b289c3cc0779d03d
Source dataset
uspto-grants-2014_01
Patent number
US08623860B2

Reaction notes

Loading…