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Potassium Carbonate → 2-(5-bromo-3-methyl-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)acetamide

HRID 58042
Notes
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Reaction equation

HRID 58042 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.Br[CH2:12][C:13]([NH2:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH2:12][C:13]([NH2:15])=[O:14])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 732761-Methyl-5-bromouracil

Product 1

HCID 897817662-(5-bromo-3-methyl-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-bromo-1-methylpyrimidine-2,4(1H,3H)-dione (200 mg, 0.976 mmol), 2-bromoacetamide (162 mg, 1.171 mmol) and K2CO3 (162 mg, 1.171 mmol) in DMSO (4 mL) was stirred at room temperature for 4 hours. The reaction mixture was subsequently filtered and purified via preparative HPLC, eluting with a gradient of 1-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give the title compound.

Workup

  1. filtrationThe reaction mixture was subsequently filtered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 1-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-55ff6c7d81534e98b295d92b9e624b09
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434743B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes