Methanol → 4,6-Dimethoxy-2-methylpyrimidin-5-amine

HRID 1628507Notes

Reaction equation

HRID 1628507 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([NH2:11])=[C:9](Cl)[N:8]=[C:7]([CH3:13])[N:6]=1.[CH3:14][OH:15]>>[CH3:1][O:2][C:5]1[C:10]([NH2:11])=[C:9]([O:15][CH3:14])[N:8]=[C:7]([CH3:13])[N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amineHCID 10942334Sodium Methoxide

Product 1

HCID 212392004,6-Dimethoxy-2-methylpyrimidin-5-amineYield 100%

Conditions

Temperature
70 °C

Procedure

Sodium methoxide (28% solution in methanol, 150 mL) was added dropwise to a stirred solution of 4,6-dichloro-2-methylpyrimidin-5-amine (15.0 g, 84.3 mmol) in methanol (150 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr, at 70° C. for 6 hr. The mixture was concentrated, diluted with aqueous saturated ammonium chloride and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (14.2 g, 84.3 mmol, 100%).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with aqueous saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63a004bd402445b68b0cddc25f7818f6
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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