2-Propylimidazole → 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-2-chloro-6-(2-propylimidazol-1-yl)purine

HRID 2264867Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([Cl:29])=[N:23][C:24]=2Cl)(=[O:3])[CH3:2].[CH2:30]([C:33]1[NH:34][CH:35]=[CH:36][N:37]=1)[CH2:31][CH3:32]>CC#N>[C:1]([O:4][C@@H:5]1[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([Cl:29])=[N:23][C:24]=2[N:34]1[CH:35]=[CH:36][N:37]=[C:33]1[CH2:30][CH2:31][CH3:32])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloropurine (1.12 g, 2.5 mmol) and 2-propylimidazole (2.20 g, 20 mmol) was dissolved in CH3CN (30 mL) and stirred at 65° C. under N2 for 2 h (reaction complete, TLC). After removal of volatiles, the residue was dissolved in CH2Cl2 (200 mL) and washed (H2O, 3×50 mL). The aqueous phase was extracted with CH2Cl2, and the combined organic phase was dried (Na2SO4) and evaporated to dryness. The residue was chromatographed (MeOH/CH2Cl2, 1:95) to give 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(2-propylimidazol-1-yl)purine (977 mg, 93%).

Workup

custom(reaction complete, TLC)
customAfter removal of volatiles
dissolutionthe residue was dissolved in CH2Cl2 (200 mL)
washwashed (H2O, 3×50 mL)
extractionThe aqueous phase was extracted with CH2Cl2
dry with materialthe combined organic phase was dried (Na2SO4)
customevaporated to dryness
customThe residue was chromatographed (MeOH/CH2Cl2, 1:95)

Sources & evidence

ORD record: ord-040e3dec56f440ec8c836c7b742e622b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855285B2

Reaction notes

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