Imidazole → HCID 22878324, compound

HRID 1489356Notes

Reaction equation

HRID 1489356 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15]O)[O:12][C@@H:11]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:50]I>C(#N)C.CCOCC>[I:50][CH2:15][CH2:14][C@H:13]1[O:12][C@@H:11]([N:17]2[CH:25]=[C:23]([CH3:24])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:10][C@@H:9]1[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 15331970HCID 15331970, compound

Product 1

HCID 22878324HCID 22878324, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3'-O-t-butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine prepared according to the method of Example 5 (0.3 g, 0.9 mmol) in dry acetonitrile (5 ml) and ether (3.4 ml) were added 3 eq of triphenyl phosphine (0.7 g, 2.8 mmol), 4 eq of imidazole (0.3 g, 3.7 mmol) and 2.2 eq of iodine (0.5 g, 2.8 mmol). The reaction mixture was stirred for 45 min and the solvent was evaporated. Ethyl acetate was added to the residue and the residue washed with water, saturated sodium chloride and dried with sodium sulfate. The title compound was purified by flash chromatography using a 30-50% gradient of ethyl acetate in hexane. The yield was 90%.

Workup

  1. customthe solvent was evaporated
  2. additionEthyl acetate was added to the residue
  3. washthe residue washed with water, saturated sodium chloride
  4. dry with materialdried with sodium sulfate
  5. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-7ffa75dfa9324d1aba5d4a4fe81c39ba
Source dataset
uspto-grants-1997_10
Patent number
US05677439

Reaction notes

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