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

HRID 1779308Notes

Reaction equation

HRID 1779308 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-e536eaa2878b4b0eb7d950f7e6a55d03
Source dataset
uspto-grants-1997_05
Patent number
US05627137

Reaction notes

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