Methyl 2-chloro-6-methylpyrimidine-4-carboxylate → Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate

HRID 2264158Notes

Reaction equation

HRID 2264158 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 2

HCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 19018471Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1 g of methyl 2-chloro-6-methylpyrimidine-4-carboxylate, 20 mL of methanol and 2 mL of 30% sodium methoxide in methanol was stirred under nitrogen at room temperature for 3 hrs, quenched with 3 mL of acetic acid and concentrated under reduced pressure. The residue was partitioned between 25 mL of saturated sodium bicarbonate and 3×20 mL of ethyl acetate and the extracts dried over MgSO4. Concentration under reduced pressure gave a white crystalline solid: MS (m+1)=183.1; 1H NMR (400 MHz, CDCl3) 7.5 (s, 1H), 4.1 (s, 3H), 4.0 (s, 3H), 2.58 (s, 3H).

Workup

  1. customquenched with 3 mL of acetic acid
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between 25 mL of saturated sodium bicarbonate and 3×20 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-66031a05914e4566b3f18994f1918297
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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