Trifluoroacetic acid methylene chloride → N-(4-(Dipropylphosphoryl)phenyl)-2-isopropyl-9H-purin-6-amine

HRID 655806Notes

Reaction equation

HRID 655806 reaction equation
[CH2:1]([P:4]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3C2CCCCO2)=[CH:11][CH:10]=1)([CH2:6][CH2:7][CH3:8])=[O:5])[CH2:2][CH3:3].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH2:1]([P:4]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][NH:20]3)=[CH:11][CH:10]=1)([CH2:6][CH2:7][CH3:8])=[O:5])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68928723N-(4-(Dipropylphosphoryl)phenyl)-2-isopropyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 178460695N-(4-(Dipropylphosphoryl)phenyl)-2-isopropyl-9H-purin-6-amine

Procedure

N-(4-(Dipropylphosphoryl)phenyl)-2-isopropyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (0.23 g) was added 50%/50% TFA/DCM (6 mL) and the resulting solution was stirred at rt for 15 min. HPLC showed the completion of the reaction. Solvent was removed on a rotavapor. The residue was dissolved in 30 mL ethyl acetate and the organic solution was washed 5% NaHCO3 (10 mL), brine (10 mL) and dried over anhydrous Na2SO4. The final product was obtained by flash column chromatography on silica gel (10% MeOH/DCM).

Workup

  1. customthe completion of the reaction
  2. customSolvent was removed on a rotavapor
  3. dissolutionThe residue was dissolved in 30 mL ethyl acetate
  4. washthe organic solution was washed 5% NaHCO3 (10 mL), brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-13f33f073cbd4ee8a05e987e0fd1ed49
Source dataset
uspto-grants-2011_12
Patent number
US08071609B2

Reaction notes

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