Acetic Acid → 9-Benzyl-2,6-dichloro-9H-purine

HRID 1080670Notes

Reaction equation

HRID 1080670 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C>CS(C)=O>[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:10]([Cl:17])[N:9]=1.[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 53244122,6-Dichloropurine

Product 2

HCID 2366419-Benzyl-2,6-dichloro-9H-purineHCID 2452637-benzyl-2,6-dichloro-7H-purine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 4.56 potassium carbonate and 5.67 g of 2,6-dichloropurine in 40 ml of dimethylsulfoxide was added, 5.64 g of benzylbromide. The mixture was stirred for 45 minutes under nitrogen at room temperature and was then poured onto crushed ice. The pH of the mixture was adjusted to 5 with acetic acid and extracted with methylene chloride (2×400 ml). The combined extracts were washed with water (6×400 ml), and brine (1×400 ml), dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel using chloroform-methanol (9:1-V:V) as the eluent to give 3.59 g of 2,6-dichloro-9-benzylpurine, m.p. 152°-152.5° C. and 1.32 g of 2,6-dichloro-7-benzylpurine, m.p. 151°-151.5° C.

Workup

  1. additionwas added
  2. additionwas then poured
  3. customonto crushed ice
  4. extractionextracted with methylene chloride (2×400 ml)
  5. washThe combined extracts were washed with water (6×400 ml), and brine (1×400 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-87afa55893284dd2af6909855e7ce574
Source dataset
uspto-grants-1996_12
Patent number
US05583137

Reaction notes

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