Ethyl Acetate → HCID 68701666, compound

HRID 1799466Notes

Reaction equation

HRID 1799466 reaction equation
[NH:1]1[CH:9]=[C:7]([NH2:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1.[H-].[Na+].C(OCC)(=O)C>CS(C)=O>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:4]2[C:5](=[O:6])[C:7]([CH3:9])=[N:8][NH:1][C:2]2=[O:3])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 136115-AminouracilHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 68701666HCID 68701666, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

According to Scheme 4 Step 1: To a solution of Azathymine (300 mg, 2.36 mmol) and 4-chlorobenzyl bromide (485 mg, 2.36 mmol) in DMSO (10 mL) was added portionwise NaH (55%) (103 mg, 2.36 mmol) at room temperature under nitrogen atmosphere. The mixture was stirred for 15 min at room temperature. Ethyl Acetate was then added (150 mL) and the organic layer was extracted thrice with water (100 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford a yellow solid. The crude solid was purified by flash chromatography with silica gel using CH2Cl2/MeOH 98/2 as eluant to afford 4-(4-chlorobenzyl)-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione 8(A) (500 mg, 84%) as a white solid.

Workup

  1. extractionthe organic layer was extracted thrice with water (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford a yellow solid
  6. customThe crude solid was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-3c65dd24ccce425bbb30011a151cec75
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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