(Trimethylsilyl)imidazole → HCID 22613682, compound

HRID 844539Notes

Reaction equation

HRID 844539 reaction equation
[C:1]([CH2:3][CH:4]([C:9]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:10][CH:11]=[CH2:12])[O:5][P:6](Cl)Cl)#[N:2].C[Si](C)(C)[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>C1(C)C=CC=CC=1>[C:1]([CH2:3][CH:4]([C:9]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:10][CH:11]=[CH2:12])[O:5][P:6]([C:20]1[NH:19][CH:23]=[CH:22][N:21]=1)[C:20]1[NH:21][CH:22]=[CH:23][N:19]=1)#[N:2]

Participants

4

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 11346570HCID 11346570, compound

Product 1

HCID 22613682HCID 22613682, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To toluene (3 ml) there were added 0.578 g (2.05 mmol) of 2-cyano-1-(1,1-diethyl-3-butenyl)ethoxydichlorophosphine and 0.632 g (4.50 mmol) of 1-(trimethylsilyl)imidazole under an argon atmosphere at room temperature, and reaction was conducted for 10 minutes. After by-product chlorotrimethylsilane and toluene were removed under reduced pressure for 25 minutes at room temperature, the residual toluene and excess 1-(trimethylsilyl)imidazole were removed under reduced pressure for 2 hours at 55° C. to obtain 2-cyano-1-(1,1-diethyl-3-butenyl)ethoxybisimidazolyl phosphine as a colorless transparent oil. This was dissolved in 4.1 ml of a mixed solution of chloroform-d and chloroform, and the solution (0.5 M) was added at −3.5° C. under an argon atmosphere to 1.414 g (2.15 mmol) of N6-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′- deoxyadenosine that had been subjected to azeotropic dehydration with 5 ml of 1,4-dioxane at room temperature for one hour. Upon reaching homogeneity, the mixture was allowed to stand overnight at 4° C. for reaction to obtain the target nucleotide derivative. The 31P NMR {external standard: (CH3O)3P=140 ppm, CDCl3} was δ; 129.5, 130.3, 131.1, 134.3 ppm (measuring the 31P NMR spectrum with a 161.7 MHz NMR measuring apparatus).

Workup

  1. customreaction
  2. customAfter by-product chlorotrimethylsilane and toluene were removed under reduced pressure for 25 minutes at room temperature
  3. customthe residual toluene and excess 1-(trimethylsilyl)imidazole were removed under reduced pressure for 2 hours at 55° C.

Sources & evidence

ORD record
ord-1990d05fcf4e4bf2b6fd957f7dadee3e
Source dataset
uspto-grants-2002_04
Patent number
US06380378B1

Reaction notes

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