Potassium Carbonate → 2-Chloro-5-((2,2-difluorocyclopropyl)methoxy)pyrimidine

HRID 40571Notes

Reaction equation

HRID 40571 reaction equation
Br[CH2:2][CH:3]1[CH2:5][C:4]1([F:7])[F:6].C([O-])([O-])=O.[K+].[K+].[Cl:14][C:15]1[N:20]=[CH:19][C:18]([OH:21])=[CH:17][N:16]=1>CN(C=O)C>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([O:21][CH2:2][CH:3]2[CH2:5][C:4]2([F:7])[F:6])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 145957002-Chloro-5-pyrimidinol

Product 1

HCID 866879162-Chloro-5-((2,2-difluorocyclopropyl)methoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

295 mg (1.72 mmol) 1-bromomethyl-2,2-difluorocyclopropane and 318 mg (2.30 mmol) K2CO3 are added to a mixture of 150 mg (1.15 mmol) 2-chloro-5-hydroxypyrimidine in 2 mL DMF. The mixture is stirred at 80° C. over night. Then the reaction mixture is quenched by the addition of water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by HPLC (MeOH/H2O/NH3).

Workup

  1. customThen the reaction mixture is quenched by the addition of water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified by HPLC (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-f95e53fa1e424eae8b0b244b95016dec
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Reaction notes

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