Tin tetrachloride → HCID 68632338, compound

HRID 1869130Notes

Reaction equation

HRID 1869130 reaction equation
C(O[CH2:5][O:6][CH:7]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.[I:26][C:27]1[C:28](=[O:34])[NH:29][C:30](=[O:33])[NH:31][CH:32]=1.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:19]([O:18][CH2:17][CH:7]([O:6][CH2:5][N:31]1[CH:32]=[C:27]([I:26])[C:28](=[O:34])[NH:29][C:30]1=[O:33])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 696725-IodouracilHCID 516892Sodium BicarbonateHCID 11035330Ganciclovir Impurity 42

Product 1

HCID 68632338HCID 68632338, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol (44; prepared according to Martin J. C., Dvorak C. A., Smee D. F., Matthews T. R., Verheyden J. P. H. (1983) 9-[(1,3-Dihydroxy-2-propoxy)methyl]quanine: a new potent and selective antiherpes agent, J. Med. Chem. 26, 759-761) (2.038 g, 5.9 mmol) and 5-iodouracil (2.106 g, 8.85 mmol) in anhydrous CH2Cl2 (25 mL) at room temperature was added N,O-bis-(trimethylsilyl)acetamide (BSA, 5.46 mL, 22.13 mmol), and the mixture was stirred at room temperature under nitrogen for 2 h. The resulting clear solution was cooled to 0° C., and SnCl4 (1 M solution in CH2Cl2, 5.9 mL, 5.9 mmol) was added. The mixture was stirred at room temperature overnight, and then poured into a mixture of saturated aqueous NaHCO3 and CHCl3. The aqueous layer was extracted with CHCl3, and the combined organic phase was evaporated. The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3) to give the title compound 45 as a yellow oil (2.935 g, 95%). 1H NMR (CDCl3) δ 8.59 (s, 1H, NH), 7.82 (s, 1H, H-6), 7.36-7.26 (m, 10H, arom.), 5.28 (s, 2H, CH2N), 4.50 (s, 4H, 2 CH2), 3.99 (m, 1H, CHO), 3.52 (m, 4H, 2 CH2O).

Workup

  1. customprepared
  2. temperatureThe resulting clear solution was cooled to 0° C.
  3. stirringThe mixture was stirred at room temperature overnight
  4. extractionThe aqueous layer was extracted with CHCl3
  5. customthe combined organic phase was evaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3)

Sources & evidence

ORD record
ord-fe0f37064c9d4d99b536cc185b2c608c
Source dataset
uspto-grants-2009_12
Patent number
US07638502B2

Reaction notes

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