Water → HCID 68783685, compound

HRID 2264875Notes

Reaction equation

HRID 2264875 reaction equation
[N:1]1([C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[NH:8][CH:9]=[N:10]3)[CH:5]=[CH:4][N:3]=[CH:2]1.C(O[C@@H:19]1[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:51])[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@@H:30]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@H:20]1[O:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)C.C([O-])(O)=O.[Na+].O>CC#N>[C:22]([O:21][C@@H:20]1[C@H:30]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:40]([CH2:42][O:43][C:44](=[O:51])[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[O:41][C@H:19]1[N:10]1[CH:9]=[N:8][C:7]2[C:11]1=[N:12][CH:13]=[N:14][C:6]=2[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 516892Sodium BicarbonateHCID 10261832HCID 10261832, compound

Product 1

HCID 68783685HCID 68783685, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(Imidazol-1-yl)purine (52 mg, 0.28 mmol) was suspended in a solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (160 mg, 0.32 mmol) in dried CH3CN (10 mL). Stannic chloride (0.10 mL, 0.22 g, 0.85 mmol) was added, and the mixture very rapidly became a clear solution. The solution was stirred at ambient temperature for 4 h. NaHCO3 (0.8 g) and H2O (0.1 mL) were added sequentially, and the suspension was stirred for 1 h. The clear solution layer was separated, and the residue was extracted with CH3CN. The extracts and the solution layer were combined, and volatiles were evaporated in vacuo. The residue was chromatographed (CH2Cl2/MeOH, 1:90→1:15) to give 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-6-(imidazol-1-yl)purine (179 mg, quantitative): 1H NMR (500 MHz, CDCl3) δ 4.72 (dd, J=4.3, 12.2 Hz, 1H), 4.88 (br s, 1H), 4.95 (dd, J=3.0, 12.3 Hz, 1H), 6.29 (“t”, J=5.2 Hz, 1H), 6.47-6.50 (m, 2H), 7.24 (s, 1H), 7.35-7.60 (m, 9H), 7.93 (d, J=7.6 Hz, 2H), 8.03 (d, J=7.6 Hz, 2H), 8.07 (d, J=7.6 Hz, 2H), 8.28 (s, 1H), 8.35 (s, 1H), 8.65 (s, 1H), 9.13 (s, 1H); 13C NMR (125 MHz, CDCCl3) δ 165.0, 164.3, 164.1, 152.1, 151.5, 144.9, 142.2, 136.6, 132.9, 132.8, 132.4, 129.7, 128.8, 128.7, 128.2, 127.5, 127.2, 122.0, 116.3, 86.4, 79.9, 72.9, 70.3, 62.3; HRMS m/z 653.1749 (MNa+[C34H26N6O7Na]=653.1761).

Workup

  1. stirringthe suspension was stirred for 1 h
  2. customThe clear solution layer was separated
  3. extractionthe residue was extracted with CH3CN
  4. customvolatiles were evaporated in vacuo
  5. customThe residue was chromatographed (CH2Cl2/MeOH, 1:90→1:15)

Sources & evidence

ORD record
ord-14974071652047d8884d6a83d97f6395
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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