Sodium Methoxide → HCID 86761728, compound

HRID 2194600Notes

Reaction equation

HRID 2194600 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[N:4][C:5]([Cl:10])=[N:6][C:7]=1[CH2:8]Cl.[CH3:12][O-:13].[Na+]>CO>[Br:1][C:2]1[C:3]([Cl:11])=[N:4][C:5]([Cl:10])=[N:6][C:7]=1[CH2:8][O:13][CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86761729HCID 86761729, compound

Product 1

HCID 86761728HCID 86761728, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-2,4-dichloro-6-(chloromethyl)pyrimidine (600 mg, 2.19 mmol) in anhydrous MeOH (15 mL) at 0° C. was added NaOMe (25% wt in MeOH, 521 mg, 2.41 mmol). The mixture was stirred at 0° C. for 30 min and then allow warm to room temperature and stirred overnight. After this time the reaction mixture was concentrated in vacuo. The residue was purified using ISCO chromatography (24 g silica gel, 0-1.5% EtOAc in hexanes in 40 min) to give the title compound (480 mg, 81%) as a white solid. 1H NMR (DMSO, 300 MHz) δ 4.77 (s, 2H), 4.04 (s, 3H).

Workup

  1. temperatureallow warm to room temperature
  2. stirringstirred overnight
  3. concentrationAfter this time the reaction mixture was concentrated in vacuo
  4. customThe residue was purified
  5. customISCO chromatography (24 g silica gel, 0-1.5% EtOAc in hexanes in 40 min)

Sources & evidence

ORD record
ord-924515732f2444c0b4dd4d7b96a9b219
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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