Ammonium Hydroxide → [(E)-2-[(2R,3S,4R,5R)-5-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]vinyl]phosphonic acid

HRID 2191037Notes

Reaction equation

C([NH:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@@H:19]3[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:29])([OH:28])[OH:27])[C@@H:21]([OH:30])[C@H:20]3[OH:31])[N:17]=[CH:18][C:11]=12)(=O)C1C=CC=CC=1.[NH4+].[OH-]>>[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@@H:19]3[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:27])([OH:28])[OH:29])[C@@H:21]([OH:30])[C@H:20]3[OH:31])[N:17]=[CH:18][C:11]=12

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 59289371(E)-2-((2R,3S,4R,5R)-5-(4-benzamido-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)vinylphosphonic acid

Product 1

HCID 25152538[(E)-2-[(2R,3S,4R,5R)-5-(4-aminopyrazolo[3,4-d]pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]vinyl]phosphonic acidYield 47%

Procedure

Compound 25.2 (19.3 mg, 0.431 mmol) was treated with concentrated NH4OH (2.2 mL, 0.02 M) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was treated with 1% AcOH (2 mL). Reverse phase HPLC afforded compound 25.3 (7.0 mg, 47% yield) as a white solid: 1H NMR (D2O, 300 MHz) 8.10 (s, 2H), 6.26 (m, 1H), 6.19 (m, 1H), 5.85 (m, 1H), 4.77 (m, 1H), 4.51 (m, 1H), 4.31 (m, 1H); 31P NMR (D2O, 121.4 MHz) 9.6; MS (ESI) m/z 344 [M+H]+.

Workup

customThe solvent was removed in vacuo
additionthe residue was treated with 1% AcOH (2 mL)

Sources & evidence

ORD record: ord-2816dcf4d95a44c199f8db5b3afc033f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324179B2

Reaction notes

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