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

HRID 238149Notes

Reaction equation

HRID 238149 reaction equation
[CH2:1]([O-:3])C.[Na+].[I:5][C:6]1[C:7](Cl)=[N:8][C:9]([Cl:12])=[N:10][CH:11]=1.O>CO>[Cl:12][C:9]1[N:8]=[C:7]([O:3][CH3:1])[C:6]([I:5])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 2723922Sodium ethoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanolic sodium ethanolate solution (88.00 mL, 15.31 mmol—from 0.7 g sodium and 100 ml dry methanol) is added dropwise with stirring at −5 to 0° C. to a solution of 5-iodo-2,4-dichloropyrimidine (4.00 g, 14.55 mmol) in dry methanol (50 mL). The reaction solution is warmed to RT overnight, during which the crude product precipitates. The product is isolated by filtration and then stirred thoroughly with water (ca 50 mL) for 30 mins, recrystallised from methanol and dried over phosphorus pentoxide in the desiccator under vacuum: 2.18 g (8.06 mmol, 55.39%) of a white product.

Workup

  1. customprecipitates
  2. customThe product is isolated by filtration
  3. customrecrystallised from methanol
  4. dry with materialdried over phosphorus pentoxide in the desiccator under vacuum

Sources & evidence

ORD record
ord-0ed1c3967c30440e9ffcf51e0f376492
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Reaction notes

Loading…