Sodium Methoxide → {2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol

HRID 216168Notes

Reaction equation

HRID 216168 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:3]=1.[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57636064{2-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol2×

Product 1

HCID 57636124{2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanolYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of {2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol (6.5 g mg, 22.1 mmol, Intermediate (57)] 25 wt % sodium methoxide in MeOH (15.2 mL, 66.3 mmol), in MeOH (20 mL) is heated to 90° C. and stirred for 3 hours and concentrated by rotary evaporator to remove the solvent. The solid is dissolved in water and the solution is acidified to pH 8 with the addition of saturated ammonium chloride solution. Extracted twice with 150 mL ethyl acetate, combined the extracts, Dried over magnesium sulfate, filtered and concentrated to afford {2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol [5.66 g, 88%, Intermediate (58)] as a solid. LCMS: RT=2.35 minutes, MS: 290 (M+H).

Workup

  1. concentrationconcentrated by rotary evaporator
  2. customto remove the solvent
  3. dissolutionThe solid is dissolved in water
  4. additionthe solution is acidified to pH 8 with the addition of saturated ammonium chloride solution
  5. extractionExtracted twice with 150 mL ethyl acetate
  6. dry with materialDried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6fb9adeea9ee49dea407c4236b34c050
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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