Dimethylformamide → HCID 21833511, compound

HRID 1740849Notes

Reaction equation

HRID 1740849 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][C:9]1[C:10](=[O:22])[NH:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][C:14]=1[CH3:15].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)(Cl)Cl>[CH3:8][C:9]1[C:10]([O:22][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:11][C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:13][C:14]=1[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 135527547HCID 135527547, compound

Product 1

HCID 21833511HCID 21833511, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of sodium hydride (about 60% oily, 1.0 g) and dimethylformamide (80 ml) is added 5,6-dimethyl-2-phenyl-4(3H)-pyrimidinone (5.0 g) while the temperature of the mixture is kept at 0-5° C., and the mixture is stirred at 0° C. for 30 minutes. To the mixture is added dropwise ethyl bromoacetate (4.2 g) at the same temperature. After addition, the mixture is stirred at 80° C. for three hours, and thereto are added ice-water and chloroform. The chloroform layer is collected by filtration, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from isopropanol to give ethyl 2-(5,6-dimethyl-2-phenyl-4-pyrimidinyloxy)acetate (6.2 g), m.p. 90-91° C.

Workup

  1. customis kept at 0-5° C.
  2. additionAfter addition
  3. stirringthe mixture is stirred at 80° C. for three hours
  4. filtrationThe chloroform layer is collected by filtration
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-d6f8631367d342199d8911d4cecc0e5d
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

Loading…