Methanol → 4-Chloro-2,6-dimethoxypyrimidine

HRID 426249Notes

Reaction equation

HRID 426249 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH3:10][O-:11].[Na+].[CH3:13][OH:14]>>[Cl:9][C:4]1[CH:5]=[C:6]([O:11][CH3:10])[N:7]=[C:2]([O:14][CH3:13])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 773782,4,6-TrichloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 806004-Chloro-2,6-dimethoxypyrimidineYield 98.4%

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask, 2,4,6-trichloro-pyrimidine (11.41 g, 62.2 mmol) was dissolved in 140 mL MeOH. The flask was cooled to 0° C. NaOMe (25% in MeOH, 28.44 mL, 124.4 mmol) was added to the flask dropwise (in 30 minutes). The reaction was stirred at 0° C. for 2 hours, then was warmed up to room temperature for 1 hour. The reaction mixture was concentrated down. Ethyl acetate was added, followed by washing with water. The organic layer was concentrated down after drying over anhydrous sodium sulfate to give white solid (10.68 g, 98.4%). LC-MS shows 175.1 (M+1). 1H NMR (300 MHz, CDCl3): δ 6.52 (s, 1H), 4.0 (s, 6H); 13C NMR (300 MHz, CDCl3): δ 172.55, 164.96, 161.03, 99.94, 54.42, 53.76.

Workup

  1. temperaturewas warmed up to room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated down
  3. additionEthyl acetate was added
  4. washby washing with water
  5. concentrationThe organic layer was concentrated down
  6. dry with materialafter drying over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-71dbb98776e243d4a3755706585b68e7
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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