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

HRID 38218Notes

Reaction equation

HRID 38218 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-dbd9c77086494889833e3e4e2dc868d4
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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