Iodine → 3052-06-0

HRID 1869129Notes

Reaction equation

HRID 1869129 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[I:18]I.[N+]([O-])(O)=O>C(Cl)(Cl)Cl>[C@@H:1]1([N:10]2[CH:17]=[C:16]([I:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 807IodineHCID 944Nitric AcidHCID 18323Uracil Arabinoside

Product 1

HCID 966213052-06-0Yield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 15 (1.2 g, 4.9 mmol), iodine (1.50 g, 5.9 mmol), CHCl3 (6 mL), and 1 N HNO3 (24 mL) was heated at reflux for 2 hours, and then cooled. The crystalline solid was collected by filtration and washed with ether to give the title compound 16 as a white solid (1.12 g, 62%). 1H NMR (DMSO-d6) δ 11.6 (s, 1H, NH), 8.10 (s, 1H, H-6), 5.95 (d, 1H, H-1′), 5.52 (br, 1H, OH), 5.40-5.10 (br, 1H, OH), 4.15-3.90 (m, 2H, H-2′, H-3′), 3.80-3.60 (m, 3H, H-4′, H-5′), 3.60-3.30 (m, 1H, OH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. filtrationThe crystalline solid was collected by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-56332324983d438e98a037e25511b7bb
Source dataset
uspto-grants-2009_12
Patent number
US07638502B2

Reaction notes

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