Dimethyl Sulfoxide → N-(Hexahydro-1,5-dimethyl-2,4,6-trioxo-5-pyrimidinyl)-2,3,4,5-tetrafluorobenzamide

HRID 1097278Notes

Reaction equation

HRID 1097278 reaction equation
Cl.[NH2:2][C:3]1([CH3:13])[C:8](=[O:9])[N:7]([CH3:10])[C:6](=[O:11])[NH:5][C:4]1=[O:12].[F:14][C:15]1[C:16]([F:28])=[C:17]([F:27])[C:18]([F:26])=[C:19]2C(=O)O[C:21](=[O:22])[C:20]=12.CCN(CC)CC.CS(C)=O>O>[CH3:10][N:7]1[C:8](=[O:9])[C:3]([NH:2][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([F:26])[C:17]([F:27])=[C:16]([F:28])[C:15]=2[F:14])([CH3:13])[C:4](=[O:12])[NH:5][C:6]1=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 69545Tetrafluorophthalic anhydrideHCID 66811031HCID 66811031, compound

Product 1

HCID 24765565N-(Hexahydro-1,5-dimethyl-2,4,6-trioxo-5-pyrimidinyl)-2,3,4,5-tetrafluorobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
153 °C

Procedure

A mixture of 5-amino-1,5-dimethylbarbituric acid hydrochloride (0.42 g, 2 mmol), tetrafluorophthalic anhydride (0.44 g, 2 mmol), Et3N (0.28 mL, 0.20 g, 2 mmol) and DMSO (3 mL) was stirred and heated at 153° C. for 5 hours. The reaction mixture was then allowed to cool down to room temperature and poured into water (10 mL). The oil that immediately formed was carefully removed from the solution, from which a solid precipitated after 4 days standing at room temperature. The precipitate was collected by filtration, washed with water and dried under reduced pressure to give 20a as yellow crystals.

Workup

  1. temperatureto cool down to room temperature
  2. customThe oil that immediately formed
  3. customwas carefully removed from the solution, from which a solid
  4. customprecipitated after 4 days
  5. customstanding at room temperature
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-63e15b5ce3de44278155a60744c3de3c
Source dataset
uspto-grants-2012_03
Patent number
US08143252B2

Reaction notes

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