5-Allyl-4-chloro-6-(2,4-dichloroanilino)-2-methylpyrimidine → 4-Chloro-1-(2,4-dichlorophenyl)-6-methyl-5,7-diazaindole

HRID 1860436Notes

Reaction equation

HRID 1860436 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([C:10]1[C:11]([Cl:26])=[N:12][C:13]([CH3:25])=[N:14][C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[CH:8]=C.CC(C)=O.O>C(O)(C)(C)C.O.S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Cl:26][C:11]1[N:12]=[C:13]([CH3:25])[N:14]=[C:15]2[C:10]=1[CH:7]=[CH:8][N:16]2[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24]

Participants

8

Reactant 3

HCID 121134695-Allyl-4-chloro-6-(2,4-dichloroanilino)-2-methylpyrimidineHCID 18366337Propan-2-one--water (1/1)HCID 23667635Sodium periodate

Product 1

HCID 121134704-Chloro-1-(2,4-dichlorophenyl)-6-methyl-5,7-diazaindoleYield 50.4%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

Sodium periodate (3.83 g, 17.9 mmol) was added to a stirred solution of (11) (1.94 g, 5.90 mmol) in 3:1 acetone-water (55 mL). The mixture was heated briefly to obtain homogeneity, and a 2.5% solution of osmium tetroxide in t-butanol (0.4 mL) was added. After 20 h, the mixture was diluted with water (50 mL) and saturated sodium thiosulfate (50 mL), and extracted with ethyl acetate. The combined extracts were concentrated under vacuum, and the residue was stirred in dichloromethane (40 mL) and 4 N HCl (5 mL) for 4 h. The mixture was poured into saturated NaHCO3, extracted with dichloromethane, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed (elution with dichloromethane) to afford 0.929 g (50%) of diazaindole (12) as a white solid.

Workup

  1. temperatureThe mixture was heated briefly
  2. customto obtain homogeneity
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined extracts were concentrated under vacuum
  5. wait4 N HCl (5 mL) for 4 h
  6. additionThe mixture was poured into saturated NaHCO3
  7. extractionextracted with dichloromethane
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed
  11. wash(elution with dichloromethane)

Sources & evidence

ORD record
ord-6002bbc464ed4743b8b2999dd95424ef
Source dataset
uspto-grants-2003_03
Patent number
US06531475B1

Reaction notes

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