Chlorotrimethylsilane → 2,6-Dichloropurine

HRID 969710Notes

Reaction equation

HRID 969710 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.N(OCCC(C)C)=O.[Cl:23][Si](C)(C)C>[Cl-].C([N+](CC)(CC)CC)C>[Cl:23][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

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8053Isoamyl NitriteHCID 10149094HCID 10149094, compound

Product 1

HCID 53244122,6-DichloropurineYield 78.5%

Reagents, catalysts & solvents 1

HCID 5946Tetraethylammonium ChlorideCatalyst

Conditions

Temperature
55 °C

Procedure

9-Acetyl-2-amino-6-chloropurine (0.50 g, 2.36 mmol), tetraethylammonium chloride (0.025 g, 0.15 mmol) and isoamyl nitrite (0.42 g, 3.54 mmol) were added to chlorotrimethylsilane (4.0 g, 36.8 mmol), and the mixture was heated to 50-60° C. and stirred for 10 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 2,6-dichloropurine as a white powder (0.35 g, yield 78.3%). The properties of the obtained compound were the same as in Example 1(2).

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-bb49f1bde22b487c8c4ff306dbe3e3d5
Source dataset
uspto-grants-2007_12
Patent number
US07307167B2

Reaction notes

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