Water → 2-Chloro-5-iodo-4-methoxypyrimidine

HRID 2284786Notes

Reaction equation

HRID 2284786 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([I:9])=[CH:4][N:3]=1.C[O-].[Na+].O.[C:14](OCC)(=[O:16])C>O1CCCC1.CN(C)C=O.CO>[Cl:1][C:2]1[N:7]=[C:6]([O:16][CH3:14])[C:5]([I:9])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 151888882-Chloro-5-iodo-4-methoxypyrimidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-5-iodopyrimidine (500 mg) in tetrahydrofuran (4 mL) and N,N-dimethylformamide (4 mL), a 5.0 mol/L a solution of sodium methoxide in methanol (360 μL) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate to obtain 2-chloro-5-iodo-4-methoxypyrimidine (Q1, 460 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-0b3a10deb6944dcb8f5c35c7b733b4aa
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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