HCID 22613676, compound → HCID 178444923, compound

HRID 844535Notes

Reaction equation

HRID 844535 reaction equation
[C:1]([CH2:3][CH:4]([CH2:9][CH2:10][CH3:11])[O:5][P:6](Cl)Cl)#[N:2].C[Si]([C:16]1[NH:17][CH:18]=[C:19]([CH3:21])[N:20]=1)(C)C>C1(C)C=CC=CC=1>[C:1]([CH2:3][CH:4]([CH2:9][CH2:10][CH3:11])[O:5][P:6]([C:16]1[NH:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:16]1[NH:17][CH:18]=[C:19]([CH3:21])[N:20]=1)#[N:2]

Participants

4

Reactant 2

HCID 22613676HCID 22613676, compoundHCID 178430902HCID 178430902, compound

Product 1

HCID 178444923HCID 178444923, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To toluene (5 ml) there were added 0.267 g (1.25 mmol) of 2-cyano-1-n-propylethoxydichlorophosphine and 0.425 g (2.75 mmol) of trimethylsilyl-4-methylimidazole under an argon atmosphere at room temperature, and reaction was conducted for 5minutes. After by-product chlorotrimethylsilane and toluene were removed under reduced pressure for 10 minutes at room temperature, the residual toluene and excess trimethylsilyl-4-methylimidazole were removed under reduced pressure for 2 hours at 35° C. to obtain 2-cyano-1-n-propylethoxybis (4-methylimidazolyl)phosphine as a colorless transparent oil. This was dissolved in 2.5 ml of chloroform-d, and the solution (0.5 M) was added to 0.678 g (1.25 mmol) of 5′-O-(4,4′-dimethoxytrityl)thymidine that had been dried under reduced pressure for 2 hours, under an argon atmosphere at room temperature. Upon reaching homogeneity, the mixture was allowed to stand overnight for reaction to obtain a phosphorazolide compound represented by the formula (1-18) above.

Workup

  1. customreaction
  2. customAfter by-product chlorotrimethylsilane and toluene were removed under reduced pressure for 10 minutes at room temperature
  3. customthe residual toluene and excess trimethylsilyl-4-methylimidazole were removed under reduced pressure for 2 hours at 35° C.

Sources & evidence

ORD record
ord-b1d79882e29f4c0d93539d8e42bff6a5
Source dataset
uspto-grants-2002_04
Patent number
US06380378B1

Reaction notes

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