Diiodomethane → HCID 12042956, compound

HRID 1446035Notes

Reaction equation

HRID 1446035 reaction equation
[C:1]([NH:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[C@@H:18]([O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:17]2)=[C:9](N)[N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(ON=O)CCCC.[I:43]CI.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([NH:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@@H:16]2[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[C@@H:18]([O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:17]2)=[C:9]([I:43])[N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 10026Pentyl nitriteHCID 24437Sodium Sulfite2×HCID 12042955HCID 12042955, compound

Product 1

HCID 12042956HCID 12042956, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

2-isobutyrylamino-6-amino-9-(2-deoxy-3,5-di-O-isobutyryl-β-D-ribofuranosyl]purine (17) [Babara L. Gaffney, Luis A. Marky and Roger A. Jones, Tetrahedron, 40, 3-13 (1984)] 2.38 g (5 mmol) was heated at 60° C. under argon atmosphere. n-pentylnitrite 13.5 ml (0.10 mol) and diiodomethane 25 ml (0.31 mol) were rapidly added and suspended. The mixture was irradiated by visible light using 200 W halogen tungsten lump at the distance from light source 2 cm for 3 hours under well stirring at 60° C. To the reaction mixture, saturated aqueous sodium sulfite 30 ml was added and stirred at room temperature for 3 hours. Thereafter, saturated aqueous sodium sulfite 120 ml and chloroform 150 ml were added to separate the layers. The aqueous layer was extracted twice with chloroform. The thus obtained organic layer was dried with anhydrous magnesium sulfate and concentrated. The residue was purified by short column (developer: ethyl acetate:dichloromethane=1:4) to obtain the product (18) 1.01 g (1.72 mmol) (34.4%).

Workup

  1. customThe mixture was irradiated by visible light
  2. customfor 3 hours
  3. stirringstirred at room temperature for 3 hours
  4. customto separate the layers
  5. extractionThe aqueous layer was extracted twice with chloroform
  6. dry with materialThe thus obtained organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by short column (developer: ethyl acetate:dichloromethane=1:4)

Sources & evidence

ORD record
ord-6945b59751ea48a6a571d4d522d1ba60
Source dataset
uspto-grants-2010_02
Patent number
US07667031B2

Reaction notes

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