Ethyl oxoacetate → 2,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

HRID 2105140Notes

Reaction equation

HRID 2105140 reaction equation
[Na].[NH2:2][C:3]1[C:4]([SH:11])=[N:5][C:6]([SH:10])=[N:7][C:8]=1[NH2:9].[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br.C([O:26][CH2:27][CH3:28])(=O)C=O>CO>[F:12][C:13]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][S:10][C:6]1[N:5]=[C:4]([S:11][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:13]=2[F:12])[C:3]2[N:2]=[CH:28][C:27](=[O:26])[NH:9][C:8]=2[N:7]=1

Participants

6

Reactant 4

HCID 70211Ethyl oxoacetateHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 5360545Sodium2×HCID 178509065HCID 178509065, compound

Product 1

HCID 225060122,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (3.96 g) was dissolved in methanol (150 ml), 5,6-diamino-2,4-pyrimidinedithiol (15 g) was added, then 2,3-difluorobenzylbromide (30.9 g) slowly added and the reaction mixture was stirred at room temperature under nitrogen for 10 min. Ethyl glyoxalate (15 ml) was added followed by more sodium (2.5 g) and the reaction was left for a further 20 min. The reaction was then quenched with acetic acid (10 ml) and poured on to water (600 ml) with stirring. The resulting precipitate was filtered through celite and washed with water. The filtrate was discarded and the solid was washed through the celite using acetone. The solution was then evaporated to dryness and purified by silica gel column chromatography using 10% ethyl acetate in DCM to yield the sub-titled compound as a cream solid (8 g).

Workup

  1. waitthe reaction was left for a further 20 min
  2. customThe reaction was then quenched with acetic acid (10 ml)
  3. additionpoured on to water (600 ml)
  4. stirringwith stirring
  5. filtrationThe resulting precipitate was filtered through celite
  6. washwashed with water
  7. washthe solid was washed through the celite
  8. customThe solution was then evaporated to dryness
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3ee0dc251c54186a466e4b8017db7ff
Source dataset
uspto-grants-2009_08
Patent number
US07579342B2

Reaction notes

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