HCID 22613683, compound → HCID 178430901, compound

HRID 844536Notes

Reaction equation

HRID 844536 reaction equation
[C:1]([CH2:3][CH:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[O:5][P:6](Cl)Cl)#[N:2].C[Si]([C:17]1[NH:18][CH:19]=[C:20]([CH3:22])[N:21]=1)(C)C>C1(C)C=CC=CC=1>[C:1]([CH2:3][CH:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[O:5][P:6]([C:17]1[NH:18][CH:19]=[C:20]([CH3:22])[N:21]=1)[C:17]1[NH:18][CH:19]=[C:20]([CH3:22])[N:21]=1)#[N:2]

Participants

4

Reactant 2

HCID 22613683HCID 22613683, compoundHCID 178430902HCID 178430902, compound

Product 1

HCID 178430901HCID 178430901, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To toluene (5 ml) there were added 0.332 g (1.46 mmol) of 2-cyano-1-tert-butylethoxydichlorophosphine and 0.495 g (3.21 mmol) of trimethylsilyl-4-methylimidazole under an argon atmosphere at room temperature, and reaction was conducted for 5 minutes. 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 40° C. to obtain 2-cyano-1-tert-butylethoxybis(4-methylimidazolyl)phosphine as a colorless transparent oil. Under an argon atmosphere at room temperature, this 2-cyano-1-tert-butylethoxybis(4-methylimidazolyl)phosphine was dissolved in 2.9 ml of chloroform-d, and the solution (0.5 M) was added to 0.794 g (1.46 mmol) of 5′-O-(4,4′-dimethoxytrityl)thymidine that had been dried under reduced pressure for 2 hours. Upon reaching homogeneity, the mixture was allowed to stand overnight for reaction to obtain a nucleotide derivative represented by the formula (2-22) below. The 31P NMR of the obtained compound (external standard: (CH3O)3P=140 ppm, CDCl3) δ was 127.9, 128.2, 128.4, 130.8 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 10 minutes at room temperature
  3. customthe residual toluene and excess trimethylsilyl-4-methylimidazole were removed under reduced pressure for 2 hours at 40° C.

Sources & evidence

ORD record
ord-3a88ab67179b40239ea7c2fc9cc9255f
Source dataset
uspto-grants-2002_04
Patent number
US06380378B1

Reaction notes

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