Dichlorodimethylsilane → 2,6-Dichloropurine

HRID 969709Notes

Reaction equation

HRID 969709 reaction equation
C([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][C:7](N)=[N:8][C:9]=2[Cl:13])(=O)C.[Cl:15][Si](Cl)(C)C.N(OCCC(C)C)=O>[Cl-].C([N+](CC)(CC)CC)C.CCCCCCC>[Cl:15][C:7]1[N:6]=[C:5]2[C:10]([NH:11][CH:12]=[N:4]2)=[C:9]([Cl:13])[N:8]=1

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 8053Isoamyl NitriteHCID 10149094HCID 10149094, compound

Product 1

HCID 53244122,6-DichloropurineYield 73.8%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
55 °C

Procedure

9-Acetyl-2-amino-6-chloropurine (0.50 g, 2.36 mmol), dichlorodimethylsilane (1.01 g, 7.80 mmol), tetraethylammonium chloride (0.025 g, 0.15 mmol) and isoamyl nitrite (0.42 g, 3.54 mmol) were added to heptane (4 ml), and the mixture was heated to 50-60° C. and stirred for 14 hr. After the completion of the reaction, the mixture was filtrated. The obtained crystals were diluted with water (4.0 ml), and the mixture was adjusted to pH 4-5 with a 2M aqueous sodium hydroxide solution. After aging under ice-cooling for 1 hr, the mixture was filtrated, and the obtained crystals were dried under reduced pressure at 80° C. to give a white powder (0.31 g, yield 73.8%) of 2,6-dichloropurine.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe mixture was filtrated
  3. additionThe obtained crystals were diluted with water (4.0 ml)
  4. temperaturecooling for 1 hr
  5. filtrationthe mixture was filtrated
  6. customthe obtained crystals were dried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-a3c9ed2c2092469fbfc92b52a7f6f57a
Source dataset
uspto-grants-2007_12
Patent number
US07307167B2

Reaction notes

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