4,5-Diphenylimidazole → HCID 11628782, compound

HRID 2264872Notes

Reaction equation

HRID 2264872 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].[C:30]1([C:36]2[N:37]=[CH:38][NH:39][C:40]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[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:37]1[C:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:39]=[CH:38]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 695884,5-DiphenylimidazoleHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine

Product 1

HCID 11628782HCID 11628782, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloropurine (0.45 g, 1.0 mmol) and 4,5-diphenylimidazole (2.21 g, 10 mmol) in DMF (15 mL) was stirred at 65° C. under N2 for 67 h (reaction almost complete, TLC). Volatiles were evaporated in vacuo, and the residue was chromatographed (MeOH/CH2Cl2, 1:90) to give 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(4,5-diphenylimidazol-1-yl)purine (0.53 g, 83%) and a mixture of 4,5-diphenylimidazole (19 mg) and the title compound (52 mg, 91% total). Recrystallization (iPrOH) gave 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(4,5-diphenylimidazol-1-yl)purine: mp 146-146.5° C.; UV (MeOH) max 279 nm (∈ 18 300), min 267 nm (∈ 16 800); 1H NMR (500 MHz, CDCl3) δ 9.03 (s, 1H), 8.22 (s, 1H), 7.55-7.57 (m, 2H), 7.35-7.40 (m, 4H), 7.21-7.27 (m, 4H), 6.21 (d, J=5.5 Hz, 1H), 5.80 (“t”, J=5.6 Hz, 1H), 5.58 (“t”, J=5.1 Hz, 1H), 4.41-4.48 (m, 3H), 2.16 (s, 31), 2.15 (s, 3H), 2.09 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 170.2, 169.5, 169.4, 154.3, 153.5, 147.4, 142.9, 140.5, 139.2, 133.5, 131.1, 131.0, 128.33, 128.28, 128.17, 127.5, 127.2, 124.1, 86.4, 80.7, 73.2, 70.5, 62.9, 20.8, 20.5, 20.4; HRMS m/z 631.1694 (MNa+[C31H28ClN6O7Na]=631.1708). Anal. Calcd for C31H28ClN6O7: C, 59.00; H, 4.31; N, 13.32. Found: C, 58.89; H, 4.45; N, 13.24.

Workup

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

Sources & evidence

ORD record
ord-dfa91fb3350841f89fe48448c2dbd01f
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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