Methyl 2,4-dichloropyrimidine-6-carboxylate → methyl 2-chloro-6-methoxypyrimidine-4-carboxylate

HRID 488458Notes

Reaction equation

HRID 488458 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[O-:13][CH2:14]C.[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([O:13][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 2723922Sodium ethoxide

Product 1

HCID 312614methyl 2-chloro-6-methoxypyrimidine-4-carboxylateYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2,6-dichloropyrimidine-4-carboxylate (10 g) (M. Winn et. al., J.Med.Chem. 36 (18), (1993), 2676-2688) in methanol (100 ml) was treated with sodium ethoxide (3 g) and left for 16 hours. Methanol was evaporated and the residue partitioned between dichloromethane and saturated aqueous NaHCO3. The organic was washed with brine, dried and evaporated to give the title compound (24%). NMR δ(CDCl3) 4.00(3H, s), 4.07(3H, s), 7.37(1H, s). (b) Sodium 2-chloro-6-methoxypyrimidine-4-carboxylate

Workup

  1. customMethanol was evaporated
  2. customthe residue partitioned between dichloromethane and saturated aqueous NaHCO3
  3. washThe organic was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4791d1cb02ce455081505e082f29a776
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Reaction notes

Loading…