Imidazole → HCID 18345597, compound

HRID 2301681Notes

Reaction equation

HRID 2301681 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([CH2:17][O:18][C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][C@H:12]1[OH:13].[NH:38]1[CH:42]=[CH:41][N:40]=[CH:39]1.[S:43](Cl)(Cl)(=[O:45])=[O:44].O>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([CH2:17][O:18][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:14][C@H:12]1[O:13][C:39]1[N:38]=[CH:42][C:41](=[S:43](=[O:45])=[O:44])[N:40]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24648Sulfuryl chlorideHCID 11762978HCID 11762978, compound

Product 1

HCID 18345597HCID 18345597, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-35 °C

Procedure

604 mg (1.18 mmols) of 6-chloro-9-[3-deoxy-5-O-(triphenylmethyl)-β-D-erythro-pentofuranosyl]-9H-purine was dissolved in 11.8 ml of methylene chloride, to which was added 486 mg (7.07 mmols) of imidazole. This reaction mixture was cooled to −35° C., to which was added 0.15 ml (1.77 mmols) of sulfuryl chloride, and stirred for 30 minutes. Then, after having been restored to be at room temperature, this was stirred overnight. To the reaction mixture, water was added to stop the reaction. Then, the mixture was separated into layers, and the aqueous layer was washed with dichloromethane. The organic layers were combined together, dried with anhydrous sodium sulfate, and filtered. The solvent was evaporated from the resulting filtrate. The residue was purified through silica gel column (silica 40 g), using 33 to 50% hexane/ethyl acetate, to obtain 570 mg (yield 75.0%) of the intended product, which was colorless oil.

Workup

  1. customto be at room temperature
  2. stirringthis was stirred overnight
  3. customthe reaction
  4. customThen, the mixture was separated into layers
  5. washthe aqueous layer was washed with dichloromethane
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated from the resulting filtrate
  9. customThe residue was purified through silica gel column (silica 40 g)

Sources & evidence

ORD record
ord-9ad434b096bd42d0a57b335415c268ae
Source dataset
uspto-grants-2002_12
Patent number
US06500946B1

Reaction notes

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