Iodoethane → HCID 23504768, compound

HRID 1884905Notes

Reaction equation

HRID 1884905 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](I)[CH3:25]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:24][CH3:25])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium Carbonate2×HCID 10658048HCID 10658048, compound

Product 1

HCID 23504768HCID 23504768, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A one liter flask is charged with 25.5 g of 2chloro-6-(phenyl-amino)-purine (104 mmol), 16.7 g of K2CO3 (121 mmoles) and 500 ml of DMF. The mixture is stirred for one hour to solubilize K2CO3, followed by addition of ethyliodid (16.1 ml, 200 mmoles). The flask is stirred at RT for 2 hours under argon. Upon completion, the solvent is removed by evaporation under reduced pressure, and the remaining powder is extracted with 150 ml of ethyl acetate, washed with water (3×30 ml) and with 30 ml of a saturated NaCl soln. The aqueous layers are extracted with ethyl acetate (2×150 ml). The combined organic layers are dried (MgSO4), filtered and concentrated. The crude product is stirred with 100 ml of diethyl ether to give a crude yellow powder, which is filtered and dried at 50° C. under HV. 23.08 g (84 mmol, 81% yield) of 2-chloro-9-ethyl-6-(phenyl-amino)-9H-purine are obtained as a white crystalline powder. Rf=0.65 (CH2Cl2/MeOH (95/5); m.p. 158° C.; ESI-MS: 274 (M+H)+; 1H-NMR (d6-DMSO, 200 MHz, TMS): 1.4 ppm (t, 3H, J1=7 Hz, H1), 4.2 ppm (q, 2H, J1=7 Hz, H2), 7.1 ppm (t, 1H, J2=8 Hz, H7), 7.4 ppm (t, 2H, J2=8 Hz, H6), 7.85 ppm (d, 2H, J2=8 Hz, H5), 8.3 ppm (s, 1H, H3), 10.3 ppm (s, 1H, H4).

Workup

  1. stirringThe flask is stirred at RT for 2 hours under argon
  2. customUpon completion, the solvent is removed by evaporation under reduced pressure
  3. extractionthe remaining powder is extracted with 150 ml of ethyl acetate
  4. washwashed with water (3×30 ml) and with 30 ml of a saturated NaCl soln
  5. extractionThe aqueous layers are extracted with ethyl acetate (2×150 ml)
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. stirringThe crude product is stirred with 100 ml of diethyl ether
  10. customto give a crude yellow powder, which
  11. filtrationis filtered
  12. customdried at 50° C. under HV

Sources & evidence

ORD record
ord-ab4a2d8671b94a17a781e94cf44420ba
Source dataset
uspto-grants-2004_07
Patent number
US06767906B2

Reaction notes

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