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Dimethylformamide → Methyl 5-(benzyloxy)-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1409587
Notes
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Reaction equation

HRID 1409587 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]([S:10][CH3:11])=[N:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCOC(C)=O>[CH3:15][O:14][C:12]([C:3]1[N:4]=[C:5]([S:10][CH3:11])[N:6]([CH3:9])[C:7](=[O:8])[C:2]=1[O:1][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86710284Methyl 5-hydroxy-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 86710286Methyl 5-(benzyloxy)-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylateYield 18.7%

Reagents, catalysts & solvents

1
HCID 8857Ethyl AcetateSolvent

Procedure

In a round-bottomed flask, methyl 5-hydroxy-1-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (55.0 g, 239 mmol) and potassium carbonate (33.0 g, 239 mmol) were combined with DMF (200 ml) to give a black suspension. Benzyl bromide (40.9 g, 239 mmol) was added and the resulting mixture was stirred at room temperature for 3.5 days. The reaction was quenched by the addition of cold water. The mixture was filtered to provide a brown solid. Chromatography (SiO2; 10% to 50% EtOAc in hexanes) provided the desired product as an off-white solid (14.3 g; 18%). LCMS: m/z=321 (MH+).

Workup

  1. customto give a black suspension
  2. customThe reaction was quenched by the addition of cold water
  3. filtrationThe mixture was filtered
  4. customto provide a brown solid

Sources & evidence

ORD record
ord-8932bdcdba504449856d18768f8bb737
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921388B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes