Sodium hydride → 5-Bromo-2-(cyclopropylmethoxy)pyrimidine

HRID 633731Notes

Reaction equation

HRID 633731 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[Br:8][C:9]1[CH:10]=[N:11][C:12](Cl)=[N:13][CH:14]=1>C1COCC1.O>[Br:8][C:9]1[CH:10]=[N:11][C:12]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 638684135-Bromo-2-(cyclopropylmethoxy)pyrimidineYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 607.92 mg (15.20 mmol) of sodium hydride in 50 mL of THF is prepared under argon. A solution of 1.10 g (15.20 mmol) of cyclopropanemethanol in 5 mL of THF is added dropwise. The mixture is stirred for 50 minutes at room temperature. 1 g (5.07 mmol) of 5-bromo-2-chloropyrimidine in 5 mL of THF is then added. The mixture is stirred at room temperature overnight. The reaction mixture is taken up in water and extracted with ethyl acetate. The organic phase is washed with aqueous NaHCO3 solution and with saturated aqueous NaCl solution, dried and evaporated to dryness to give 1.10 g of 5-bromo-2-cyclopropylmethoxypyrimidine, corresponding to the following characteristics:

Workup

  1. customis prepared under argon
  2. stirringThe mixture is stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with aqueous NaHCO3 solution and with saturated aqueous NaCl solution
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-718e73a125124c20b5c75d72e04f5cc1
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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