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

HRID 1422474Notes

Reaction equation

HRID 1422474 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].I[CH:15]([CH3:17])[CH3:16].O>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 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1784188752,6-dichloro-1H-purine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To 2,6-dichloro-9H-purine (a) (998 g, 5.28 mol) dissolved in anhydrous DMF (5.0 L) was added sodium hydride (60% dispersion, 254 g, 6.35 mol) with stirring at 10° C. over 1 hr. 2-iodopropane (1595 g) was added and the mixture was stirred at rt for 24 hr. Water (5.0 L) was added, and the resulting solid precipitate was collected and washed with water (500 ml) and heptane (2×2.5 L). The crude solid was crystallized from isopropyl acetate (2.1 L) to provide the title compound as a solid.

Workup

  1. stirringthe mixture was stirred at rt for 24 hr
  2. customthe resulting solid precipitate was collected
  3. washwashed with water (500 ml) and heptane (2×2.5 L)
  4. customThe crude solid was crystallized from isopropyl acetate (2.1 L)

Sources & evidence

ORD record
ord-0508444e6b154687afee9960963583ee
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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