(2R,3R,5S)-2-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-((E)-2-(diethoxyphosphoryl)vinyl)-tetrahydrofuran-3-yl benzoate → [(E)-2-[(2S,4R,5R)-5-(7-aminotriazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]vinyl]phosphonic acid

HRID 2191057Notes

Reaction equation

HRID 2191057 reaction equation
C([O:9][C@@H:10]1[CH2:14][C@@H:13](/[CH:15]=[CH:16]/[P:17]([O:22]CC)([O:19]CC)=[O:18])[O:12][C@H:11]1[N:25]1[C:29]2[N:30]=[CH:31][N:32]=[C:33]([NH2:34])[C:28]=2[N:27]=[N:26]1)(=O)C1C=CC=CC=1.C(NC1NC(=O)C2N=CN(C3C(OC(=O)C4C=CC=CC=4)CC(C=CP(O)(O)=O)O3)C=2N=1)(=O)C>>[NH2:34][C:33]1[C:28]2[N:27]=[N:26][N:25]([C@@H:11]3[O:12][C@H:13](/[CH:15]=[CH:16]/[P:17](=[O:18])([OH:19])[OH:22])[CH2:14][C@H:10]3[OH:9])[C:29]=2[N:30]=[CH:31][N:32]=1

Participants

3

Reactant 2

HCID 59289341(2R,3R,5S)-2-(7-amino-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-((E)-2-(diethoxyphosphoryl)vinyl)-tetrahydrofuran-3-yl benzoateHCID 136381446Benzoic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(2-phosphono-vinyl)-tetrahydro-furan-3-yl ester

Product 1

HCID 25152957[(E)-2-[(2S,4R,5R)-5-(7-aminotriazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]vinyl]phosphonic acidYield 76.2%

Procedure

Compound 38.2 (60 mg, 68% yield) was synthesized from compound 38.1 (115 mg, 0.24 mmol) using the procedure described for the preparation of compound 9.10. 1H NMR (D2O, 300 MHz): δ 2.31-2.55 (m, 2H), 4.78-4.98 (m, 2H), 5.78-5.88 (m, 1H), 5.94-6.08 (m, 1H), 6.23 (s, 1H). 31PNMR: 9.20 ppm. LRMS C10H13N6O5P requires 327.1. Found 327.0.

Sources & evidence

ORD record
ord-36ef217d4d854444a82cb7f34f63e6b6
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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