Methanol → 5-Isopropyl-6-chloro-2,4-dimethoxypyrimidine

HRID 1281086Notes

Reaction equation

HRID 1281086 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[C:9]([Cl:11])[C:8]([CH:12]([CH3:14])[CH3:13])=[C:7](Cl)[N:6]=1.[OH2:16].[CH3:17]O>C(OC(C)C)(C)C>[Cl:11][C:9]1[N:10]=[C:5]([O:2][CH3:1])[N:6]=[C:7]([O:16][CH3:17])[C:8]=1[CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2490092,4,6-Trichloro-5-isopropylpyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineYield 79%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

112 g of 30% sodium methoxide in methanol are added, in a 0.5 liter reactor rendered inert with nitrogen and equipped with an anchor stirrer, to the solution of compound of Example 2 (70 g, 0.31 mol) in 400 ml of isopropyl ether. The medium is kept stirred at ambient temperature. When there is no more change, 140 ml of water are added and the organic and aqueous phases are separated. The organic phase is washed with water and dried by evaporation of the solvent under vacuum. The oily residue is distilled under vacuum in order to obtain 53 g of purified 6-chloro-2,4-dimethoxy-5-(1-methylethyl)pyrimidine (oil, boiling temperature at 13 mbar=128-30° C.), which comprises approximately 5% of positional isomer.

Workup

  1. additionare added
  2. customthe organic and aqueous phases are separated
  3. washThe organic phase is washed with water
  4. customdried by evaporation of the solvent under vacuum
  5. distillationThe oily residue is distilled under vacuum in order

Sources & evidence

ORD record
ord-1cd08dd047b544f6bc3d848ae2c712f4
Source dataset
uspto-grants-2002_09
Patent number
US06452006B1

Reaction notes

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