Acetone → 1-(4,6-Dimethoxypyrimidin-2-yl)propan-2-one

HRID 1163447Notes

Reaction equation

HRID 1163447 reaction equation
[H-].[Na+].C1COCC1.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12](S(C)(=O)=O)[N:11]=1.[CH3:22][C:23]([CH3:25])=[O:24]>O>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12]([CH2:22][C:23](=[O:24])[CH3:25])[N:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 112640521-(4,6-Dimethoxypyrimidin-2-yl)propan-2-oneYield 22.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

In a reactor were placed 16.0 g (0.4 moles) of 60% sodium hydride, 400 ml of THF and 43.6 g (0.2 moles) of 4,6-dimethoxy-2-methanesulfonylpyrimidine. The reactor contents were heated to 30° C. Thereto was dropwise added 39.4 g (0.68 moles) of acetone, followed by a reaction for 2 hours. After the completion of the reaction, 350 ml of water was added and extraction with 500 ml of ethyl acetate was conducted. The ethyl acetate layer was concentrated. The concentrate was subjected to distillation under reduced pressure to obtain 8.8 g (44.9 m moles) of 1-(4,6-dimethoxypyrimidine-2-yl)-2-propanone. Refractive index n20D: 1.5181

Workup

  1. customIn a reactor were placed
  2. customfollowed by a reaction for 2 hours
  3. additionwas added
  4. extractionextraction with 500 ml of ethyl acetate
  5. concentrationThe ethyl acetate layer was concentrated
  6. distillationThe concentrate was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-86335fd3a17d466fa320dd8fbe2ebe13
Source dataset
uspto-grants-2010_10
Patent number
US07820861B2

Reaction notes

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