Trimethylphosphine → HCID 86615610, compound

HRID 1695087Notes

Reaction equation

HRID 1695087 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][N:14]=[N+]=[N-])=[C:4]([O:17][CH2:18][C:19]2[CH:32]=[CH:31][C:22]([CH2:23][NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[N:3]=1.CP(C)C>O1CCOCC1.O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][NH2:14])=[C:4]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:23][NH:24][C:25](=[O:30])[C:26]([F:27])([F:29])[F:28])=[CH:31][CH:32]=2)[N:3]=1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 58989129N-[4-(2-Amino-9-(3-azidopropyl)-purine-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 86615610HCID 86615610, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Azide 23 (Example 10, 100 mg, 0.23 mmol) is dissolved in 0.9 mL of 1,4-dioxane/H2O (8:1), and 0.3 mL of a trimethylphospine solution (1 M in THF) is added. The reaction is stirred at room temperature for 3 h, then all volatiles are removed in vacuo. The crude product is purified by flash column chromatography with dichloromethane/methanol (95:5 to 10:1). Yield: 87 mg (0.021 mmol, 91%).

Workup

  1. customall volatiles are removed in vacuo
  2. customThe crude product is purified by flash column chromatography with dichloromethane/methanol (95:5 to 10:1)

Sources & evidence

ORD record
ord-089f68b08fe543bfbdedd8c9521524ae
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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