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

HRID 58043

Reaction equation

HRID 58043 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.Cl[CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[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]([N:15]([CH3:17])[CH3:16])=[O:14])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 732761-Methyl-5-bromouracilHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 897817702-(5-bromo-3-methyl-2,6-dioxo-2,3-dihydropyrimidin-1 (6H)-yl)-N,N-dimethylacetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-bromo-1-methylpyrimidine-2,4(1H,3H)-dione (80 mg, 0.390 mmol), 2-chloro-N,N-dimethylacetamide (47.4 mg, 0.390 mmol), and potassium carbonate (64.7 mg, 0.468 mmol) in DMSO (3 mL) was stirred at room temperature 2 hours. The reaction mixture was subsequently filtered and purified via preparative HPLC, eluting with a gradient of 5-70% 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 5-70% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-4db57ee6114045f894653464c7914dd6
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Linked notes

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