Trimethylsilylacetylene → HCID 18396487, compound

HRID 612796Notes

Reaction equation

HRID 612796 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21](I)[C:19]([NH2:20])=[N:18][C:16]1=[O:17])(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35]>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])[C:19]([NH2:20])=[N:18][C:16]1=[O:17])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 18396490HCID 18396490, compound

Product 1

HCID 18396487HCID 18396487, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5'-deoxy-2',3'-di-O-acetyl-5-iodocytidine (1.35 g, 3.087 mmol) in CH2Cl2 (15 ml) there was added N,N-diisopropylethylamine (0.537 ml, 3.087 mmol), Cul (58 mg, 0.309 mmol), Pd(PPh3)2Cl2 (60 mg, 0.085 mmol), and trimethylsilyl-acetylene (0.523 ml, 3.704 mmol) at room temperature under Ar. The reaction mixture was then heated to 60° C. After stirring for 2 hours, the mixture was cooled to room temperature. The solvent was removed under reduced pressure, and the residue dissolved in EtOAc (200 ml), washed with 2% aq. EDTA.2Na, water and brine, dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure. The crude product was purified by flash chromatography on SiO2 (f2.2×25 cm, eluent: EtOAc) to give 2',3'-di-O-acetyl-5'-deoxy-5-[2-(trimethylsilyl)ethynyl]cytidine as a pale yellow solid. (1.20 g, 95% y.).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in EtOAc (200 ml)
  4. washwashed with 2% aq. EDTA
  5. dry with material2Na, water and brine, dried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customThe crude product was purified by flash chromatography on SiO2 (f2.2×25 cm, eluent: EtOAc)

Sources & evidence

ORD record
ord-d648b5ea731f4191b2f151f9d00bdda6
Source dataset
uspto-grants-1999_12
Patent number
US06005098

Reaction notes

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