Chlorotrimethylsilane → HCID 22842029, compound

HRID 1089666Notes

Reaction equation

HRID 1089666 reaction equation
[C:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)#[CH:2].Cl[Si](C)(C)C.C(N([CH2:29][CH3:30])CC)C.[C:31]1(C)[C:32]([C:37](Cl)=[O:38])=[CH:33][CH:34]=C[CH:36]=1>C(#N)C>[C:1]([C:3]1[C:4](=[O:18])[N:5]([C:37]([C:32]2[CH:33]=[CH:34][C:29]([CH3:30])=[CH:36][CH:31]=2)=[O:38])[C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)#[CH:2]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 4721725-Ethynyl-2′-deoxyuridine

Product 1

HCID 22842029HCID 22842029, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 2'-deoxy-5-ethynyluridine (J. Med. Chem., 26(5), 661-6, (1983)) (0.4 g, 1.6 mmol) in dry acetonitrile (15 ml) and chlorotrimethyl silane (0.7 ml, 5.6 mmol) was added, with ice cooling, triethylamine (1.13 ml, 8.1 mmol) and stirring was maintained at room temperature for 2.5 hr. Toluoylchloride (0.3 ml, 2.1 mmol) was then added and after stirring for a further 7 hr the mixture was filtered, the filtrate evaporated to dryness and the residue dissolved in ethanol (20 ml). Glacial acetic acid was then added and after stirring for 0.5 hr at room temperature the solvent was evaporated and residual acetic acid coevaporated with ethanol. Purification of the product by thick layer silica chromatography eluting with methanol/methylenechloride (1:24) followed by recrystallisation from methanol afforded title compound (0.03 g) melting at 176-9° C.

Workup

  1. stirringafter stirring for a further 7 hr the mixture
  2. filtrationwas filtered
  3. customthe filtrate evaporated to dryness
  4. dissolutionthe residue dissolved in ethanol (20 ml)
  5. additionGlacial acetic acid was then added
  6. stirringafter stirring for 0.5 hr at room temperature the solvent
  7. customwas evaporated
  8. customPurification of the product by thick layer silica chromatography
  9. washeluting with methanol/methylenechloride (1:24)
  10. customfollowed by recrystallisation from methanol

Sources & evidence

ORD record
ord-21a90eee434f4958a5f581319c9cea28
Source dataset
uspto-grants-1992_01
Patent number
US05079235

Reaction notes

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