Isopropyl iodide → 6-Chloro-9-isopropyl-9h-purin-2-amine

HRID 1241343Notes

Reaction equation

HRID 1241343 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[H-].[Na+].I[CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-chloro-9H-purin-2-ylamine (20 g, 0.12 moles) in DMF (200 mL) at −11° C. was added NaH (5.7 g, 0.14 moles, 60%) portionwise over 1 h. The mixture as stirred for 1 h, then 2-iodopropane (14.2 mL, 0.14 moles) was added dropwise. The solution was warmed to rt, stirred for 18 h, quenched with sat'd NH4Cl, and extracted with EtOAc. The combined extracts, were washed with water, sat'd NaCl, then dried over MgSO4 and filtered. Concentration yielded an oil which was purified by silica gel chromatography (60% EtOAc/Hexane) to a white solid (13.4 g, 54%): MS [M+H]+ 212; m.p. 135–136° C.

Workup

  1. stirringstirred for 18 h
  2. customquenched with sat'd NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts, were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationConcentration
  8. customyielded an oil which
  9. customwas purified by silica gel chromatography (60% EtOAc/Hexane) to a white solid (13.4 g, 54%)

Sources & evidence

ORD record
ord-5aadb1613e1f4cee91ad470aa1b97597
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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