4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate

HRID 2264161Notes

Reaction equation

HRID 2264161 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11]C)=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH3:15][O-:16].[Na+]>CO>[CH3:15][O:16][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 12828997Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 5 g of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate, 250 mL of methanol and 5 mL of 30% sodium methoxide in methanol was stirred under nitrogen at room temperature for 5 hrs, quenched with 10 mL of acetic acid and concentrated under reduced pressure. The residue was partitioned between 100 mL of saturated sodium bicarbonate and 200 mL of ethyl acetate and the extracts dried over MgSO4. Concentration under reduced pressure gave a white crystalline solid: MS (m+1)=215.1; 1H NMR (400 MHz, CDCl3) 8.85 (s, 1H), 4.1 (s, 3H), 4.05 (s, 3H), 3.85 (s, 3H).

Workup

  1. customquenched with 10 mL of acetic acid
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between 100 mL of saturated sodium bicarbonate and 200 mL of ethyl acetate
  4. dry with materialthe extracts dried over MgSO4
  5. concentrationConcentration under reduced pressure
  6. customgave a white crystalline solid

Sources & evidence

ORD record
ord-d43cc4563188489e99d7680de3de2f68
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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