Iodoethane → HCID 13606735, compound

HRID 1380034Notes

Reaction equation

HRID 1380034 reaction equation
[OH:1][CH2:2][CH:3]([O:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)[CH2:4][OH:5].[H-].[Na+].[H][H].[CH2:23](I)[CH3:24]>CS(C)=O.CO.O.C(Cl)Cl>[CH2:23]([N:12]1[C:13](=[O:17])[C:14]2[N:15]=[CH:16][N:8]([CH2:7][O:6][CH:3]([CH2:4][OH:5])[CH2:2][OH:1])[C:9]=2[N:10]=[C:11]1[NH2:18])[CH3:24]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 135398740GanciclovirHCID 178418361HCID 178418361, compound

Product 1

HCID 13606735HCID 13606735, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 22242641Methanol--water (1/1)Solvent2×

Procedure

To a stirred solution of 9-(1,3-dihydroxy-2-propoxymethyl)guanine (766 mg, 3.0 mmol) in sieve-dried DMSO (4 ml), under N2, was added 120 mg of 60% NaH in oil (i.e. 72 mg NaH, 3.0 mmol). Hydrogen evolution ceased and a clear solution was obtained after 10 minutes. Ethyl iodide (491 mg, 3.15 mmol) in DMSO (1 ml) was added over approximately 1 minute. The reaction was stirred overnight and then poured into CH2Cl2. The gummy precipitate was filtered off and triturated under methanol to give crystalline material. This was dissolved in MeOH--H2O (2:3) and applied to a Dowex 1×2 column (OH- form, 100 ml) packed in the same solvent. The column was developed in MeOH--H2O (2:3) and fractions containing the required product were pooled and evaporated to dryness. This residue was crystallized from methanol to give 230 mg (27% yield) of product.

Workup

  1. customa clear solution was obtained after 10 minutes
  2. filtrationThe gummy precipitate was filtered off
  3. customtriturated under methanol
  4. customto give crystalline material

Sources & evidence

ORD record
ord-3a0f05282e6247a994592f1c3a2ea854
Source dataset
uspto-grants-1986_04
Patent number
US04579849

Reaction notes

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