Methanol → Methyl(4-methoxy-5-pyrimidinyl)acetate

HRID 1888155Notes

Reaction equation

HRID 1888155 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7](Cl)=[N:8][CH:9]=[N:10][CH:11]=1)C.[Na].[CH3:15][OH:16]>>[CH3:1][O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([O:16][CH3:15])=[N:8][CH:9]=[N:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 46856293Ethyl 2-(4-chloropyrimidin-5-YL)acetate

Product 1

HCID 57907464Methyl(4-methoxy-5-pyrimidinyl)acetateYield 93%

Conditions

Temperature
120 °C

Procedure

To a solution of 0.250 g (1.25 mmol) of ethyl(4-chloro-5-pyrimidinyl)acetate (see i-20, Step A) in 10 mL of absolute methanol was dissolved 0.060 g (2.50 mmol) of sodium metal. The resulting solution was heated under microwave conditions at 120° C. for 10 min. All volatiles were removed in vacuo and the residue was diluted with saturated sodium bicarbonate and extracted with dichloromethane (3×10 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo to afford the title compound as a clear gum (0.21 g, 93%). 1H-NMR (500 MHz, CD3OD) δ: 8.72 (s, 1H), 8.35 (s, 1H), 3.96 (s, 2H), 4.01 (s, 3H), 3.70 (s, 3H), 3.57 (s,2H). LC-MS: m/z (E/S) 183 (MH)+.

Workup

  1. customAll volatiles were removed in vacuo
  2. additionthe residue was diluted with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d2792c516e264cd1be5cb969b0280775
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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