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Sodium Methoxide → 4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1624914
Notes
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Reaction equation

HRID 1624914 reaction equation
Br[C:2]1[C:3](=[O:25])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:5](=[O:16])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][OH:15])[N:7]=1.[CH3:26][O-:27].[Na+]>CN(C=O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:4]2[C:3](=[O:25])[C:2]([O:27][CH3:26])=[N:7][N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:14][OH:15])[C:5]2=[O:16])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 687025256-bromo-4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 686995764-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dioneYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

According to Scheme 2 Step 4: To a stirred solution of 6-bromo-4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.330 g, 0.79 mmol) in DMF (10 ml) was added, dropwise, at 0° C., 2M solution of sodium methoxide (0.79 mmol, 0.40 ml). The mixture was stirred 1 hour at 0° C. then quenched with water and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water then with brine, dried over MgSO4, filtered and concentrated. 270 mg (Yield=92.5%) of 4-(4-chlorobenzyl)-2-(2-(hydroxymethyl)phenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione were recovered. The product was pure enough to be used in the next step without any purification.

Workup

  1. customat 0° C.
  2. customthen quenched with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layers were successively washed with water
  5. dry with materialwith brine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29514594aebd40938916837280ddb953
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08779129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes