Diethyl Ether → 2,6-dichloro-9-(propan-2-yl)-9H-purine

HRID 2215653Notes

Reaction equation

HRID 2215653 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].I[CH:15]([CH3:17])[CH3:16].C(OCC)C>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:15]([CH3:17])[CH3:16])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 53244122,6-Dichloropurine

Product 1

HCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2,6-dichloropurine (5.00 g, 26.46 mmol) was suspended in 55 ml of dry DMF at room temperature and treated with sodium hydride, 60% dispersion (1.27 g, 31.75 mmol) added in portions. After stirring for 1 hr, 2-iodopropane (4.5 ml, 44.98 mmol) was added and the reaction stirred for 2 days. The reaction was poured into diethyl ether and washed once with saturated sodium bicarbonate solution and once with water. The mixture was dried over anhydrous sodium sulfate and concentrated in vacuo. The concentrate was chromatographed over silica gel eluting with 10% acetone in dichloromethane solution to give the desired N-9 alkylation product as a white solid.

Workup

  1. additionadded in portions
  2. stirringthe reaction stirred for 2 days
  3. washwashed once with saturated sodium bicarbonate solution and once with water
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe concentrate was chromatographed over silica gel eluting with 10% acetone in dichloromethane solution
  7. customto give the

Sources & evidence

ORD record
ord-1b733ad4bb0f4c99b7def0fc277dc3f5
Source dataset
uspto-grants-2006_09
Patent number
US07109330B2

Reaction notes

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