Trifluoroacetic acid → diethyl (E)-2-((2R,3S,4R,5R)-5-(4-benzamido-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)vinylphosphonate

HRID 2191035Notes

Reaction equation

HRID 2191035 reaction equation
[C:1]([NH:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@H:19]3[C@@H:23]4[O:24]C(C)(C)[O:26][C@@H:22]4[C@@H:21](/[CH:29]=[CH:30]/[P:31](=[O:38])([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])[O:20]3)[N:17]=[CH:18][C:11]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>O>[C:1]([NH:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@@H:19]3[O:20][C@H:21](/[CH:29]=[CH:30]/[P:31](=[O:38])([O:32][CH2:33][CH3:34])[O:35][CH2:36][CH3:37])[C@@H:22]([OH:26])[C@H:23]3[OH:24])[N:17]=[CH:18][C:11]=12)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59289330HCID 59289330, compound

Product 1

HCID 59289252diethyl (E)-2-((2R,3S,4R,5R)-5-(4-benzamido-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)vinylphosphonateYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 22.4 (163 mg, 0.299 mmol) was treated with TFA (1000 μL) and H2O (100 μL) and stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue was subjected to a silica gel column chromatography eluting with 0-20% MeOH—CH2Cl2 to afford compound 25.1 (65 mg, 43% yield) as a white solid: 1H NMR (CDCl3, 300 MHz) 9.51 (br s, 1H), 8.65 (s, 1H), 8.47 (s, 1H), 7.90 (d, J=7.5 Hz, 2H), 7.51 (t, J=7.5 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.88 (m, 1H), 6.61 (s, 1H), 5.98 (m, 1H), 4.85 (m, 1H), 4.67 (m, 1H), 4.60 (m, 1H), 3.89 (m, 4H), 1.20 (t, 6H); 31P NMR (CDCl3, 121.4 MHz) 16.6; MS (ESI) m/z 504 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. washeluting with 0-20% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-38979befeb0a4aa89febe6376db7fae1
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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