2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 11613488, compound

HRID 2264870Notes

Reaction equation

HRID 2264870 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:34]1[NH:35][CH:36]=[CH:37][N:38]=1)[CH2:31][CH2:32][CH3:33]>CC#N>[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]=2[N:35]1[CH:36]=[CH:37][N:38]=[C:34]1[CH2:30][CH2:31][CH2:32][CH3:33])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 118153512-butyl-1H-imidazole

Product 1

HCID 11613488HCID 11613488, compoundYield 115.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloropurine (2.41 g, 5.4 mmol) and 2-butylimidazole (6.68 g, 54 mmol) in CH3CN (60 mL) was stirred at 65° C. under N2 for 32 h (reaction complete, TLC). Volatiles were evaporated in vacuo, and the residue was chromatographed (MeOH/CH2Cl2, 1:90) to give crude 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(2-butylimidazol-1-yl)-2-chloropurine (3.33 g, contaminated with 2-butylimidazole): 1H NMR (500 MHz, CDCl3) δ 8.56 (s, 1H), 8.24 (s, 1H), 7.10 (s, 1H), 6.26 (d, J=5.8 Hz, 1H), 5.83 (t, J=5.6 Hz, 1H), 5.61 (t, J=5.6 Hz, 1H), 4.43-4.51 (m, 3H), 3.31 (t, J=7.9 Hz, 2H), 2.18 (s, 3H), 2.16 (s, 3H), 2.11 (s, 3H), 1.81 (quint, J=7.7 Hz, 2H), 1.50 (sext, J=7.7 Hz, 2H), 0.98 (t, J=7.3 Hz, 3H); HRMS m/z 535.1702 (MH+[C23H28ClN6O7]=535.1708).

Workup

  1. custom(reaction complete, TLC)
  2. customVolatiles were evaporated in vacuo
  3. customthe residue was chromatographed (MeOH/CH2Cl2, 1:90)

Sources & evidence

ORD record
ord-6a4b205e96244cd2870c0040c5c4c552
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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