Water → 2-(2-(4,4-Dimethyl-oxazolin-2-yl)-benzoyl)4,6-dimethoxypyrimidine

HRID 863755Notes

Reaction equation

HRID 863755 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][O:5][C:4]([C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[CH:9]([C:11]2[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=2)Br)=[N:3]1.C([O-])([O-])=[O:27].[Na+].[Na+].O>CS(C)=O>[CH3:1][C:2]1([CH3:25])[CH2:6][O:5][C:4]([C:7]2[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=2[C:9]([C:11]2[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=2)=[O:27])=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 190506432-(2-(4,4-Dimethyl-oxazolin-2-yl)-alpha-bromobenzyl)-4,6-dimethoxy pyrimidine

Product 1

HCID 190506722-(2-(4,4-Dimethyl-oxazolin-2-yl)-benzoyl)4,6-dimethoxypyrimidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.2 g of 2-(2-(4,4-dimethyl-oxazolin-2-yl)-α-bromobenzyl)-4,6-dimethoxy-pyrimidine and 2 g of Na2CO3 in 30 ml of DMSO is heated with stirring at 50°-60° C. for 3 hrs. The mixture is poured into 150 ml of water and extracted with toluene. The toluene extract is washed twice with water (2×50 ml) separated and concentrated. The thus obtained gum is chromatographed with 800 ml of 80/20 hexane/ethyl acetate, 500 ml 70/30 hexane/ethyl acetate, 60/40 ml hexane/ethyl acetate (50 ml fractions) fractions 29 to 34 yielded the title compound.

Workup

  1. temperatureis heated
  2. extractionextracted with toluene
  3. extractionThe toluene extract
  4. washis washed twice with water (2×50 ml)
  5. customseparated
  6. concentrationconcentrated
  7. customThe thus obtained gum is chromatographed with 800 ml of 80/20 hexane/ethyl acetate, 500 ml 70/30 hexane/ethyl acetate, 60/40 ml hexane/ethyl acetate (50 ml fractions) fractions 29 to 34

Sources & evidence

ORD record
ord-7618b19bba33410c9de85d308a78a6b7
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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