Thymine → HCID 18461966, compound

HRID 2303753Notes

Reaction equation

HRID 2303753 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26])=[O:19]>>[N:1]1([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][C:21]2=[O:26])=[O:19])[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3]

Participants

4

Reactant 3

HCID 1135ThymineHCID 11430Potassium CarbonateHCID 18461965HCID 18461965, compound

Product 1

HCID 18461966HCID 18461966, compoundYield 364.6%

Procedure

Thymine (630.6 mg, 5 mmol) and K2CO3 (1.38 g, 10 mmol) were combined in a 50 mL round bottom flask and azeotroped with benzene (3×10 mL). The mixture was suspended in anhydrous DMF (15 mL) under argon and allowed to stir at room temperature for 4 hours. Solid chloroacetyl piperazinone (1.37 mmol, 1.4 eq) as prepared was added, and the reaction mixture was stirred for an additional 3-4 hours. The crude reaction mixture was filtered, concentrated and precipitated by treatment with EtOAc (30 mL). The solid was washed extensively with EtOAc and dried in a dessicator under vacuum to afford 1.33g of N-(thymin-1-ylacetyl)-piperazinone (100% yield) as a white solid.

Workup

  1. customazeotroped with benzene (3×10 mL)
  2. additionwas added
  3. stirringthe reaction mixture was stirred for an additional 3-4 hours
  4. customThe crude reaction mixture
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customprecipitated by treatment with EtOAc (30 mL)
  8. washThe solid was washed extensively with EtOAc
  9. customdried in a dessicator under vacuum

Sources & evidence

ORD record
ord-f11f32779c9a4faf949904639c634d6f
Source dataset
uspto-grants-2002_08
Patent number
US06433134B1

Reaction notes

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