Dimethylformamide → 8-methyl-5-methylsulfanyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione

HRID 75638Notes

Reaction equation

HRID 75638 reaction equation
[SH:1][C:2]1[C:3]2[C:13](=[O:14])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11](=[O:21])[N:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[N:5]([CH3:9])[C:6](=[O:8])[N:7]=1.[CH3:28]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:9][N:5]1[C:4]2[N:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:11](=[O:21])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13](=[O:14])[C:3]=2[C:2]([S:1][CH3:28])=[N:7][C:6]1=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178481636HCID 178481636, compound

Product 1

HCID 597172888-methyl-5-methylsulfanyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trioneYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To crude 5-mercapto-8-methyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione 24 (100 mg) obtained in Step 5 was added N,N-dimethylformamide (0.5 ml). Under a nitrogen atmosphere, potassium carbonate (44 mg) and methyl iodide 25 (20 μl) were successively added, and the mixture was stirred at room temperature for 3 hrs. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. Anhydrous sodium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=4:1→3:1) to give 8-methyl-5-methylsulfanyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione 26 (91 mg, yield 89%) as brown crystals.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate. Anhydrous sodium sulfate
  4. filtrationwas filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (hexane:ethyl acetate=4:1→3:1)

Sources & evidence

ORD record
ord-5ddabc45f35d4839a57f82134e65a313
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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