Hydrochloric Acid → Methyl [6-(methylsulfanyl)pyrimidin-4-yl]acetate

HRID 912546Notes

Reaction equation

HRID 912546 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:9]1[CH:14]=[C:13]([S:15][CH3:16])[N:12]=[CH:11][N:10]=1)C(OC)=O.C[O-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:9]1[CH:14]=[C:13]([S:15][CH3:16])[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 57613442HCID 57613442, compound

Product 1

HCID 55265706Methyl [6-(methylsulfanyl)pyrimidin-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(6-methylsulfanyl-pyrimidin-4-yl)-malonic acid dimethyl ester 3 (3.35 g, 13 mmol) and sodium methoxide (0.300 ml of 25% w/v solution, 1.30 mmol, 0.1 eq.) in MeOH (100 ml) is heated at 60° C. for 3 hours. The reaction mixture is cooled to room temperature, neutralized with 1N HCl solution (1.30 mL) and concentrated. The residue, is extracted with ethyl acetate. The organic layer is washed with brine and dried over Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 50% to afford (6-methylsulfanyl-pyrimidin-4-yl)-acetic acid methyl ester as a yellow oil. 1H NMR 400 MHz (CDCl3) δ 8.86 (s, 1H), 7.18 (s, 1H), 3.73 (s, 3H), 3.70 (s, 2H), 2.55 (s, 3H).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. concentrationconcentrated
  3. extractionThe residue, is extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel flash chromatography
  9. washeluting with ethyl acetate in hexanes from 0% to 50%

Sources & evidence

ORD record
ord-c2225632de064640b274691410de1b90
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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