Benzoic acid 2-(6-amino-purin-9-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl ester → {2-[5-(6-Amino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acid

HRID 2191019Notes

Reaction equation

HRID 2191019 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH:15]([O:16]C(=O)C2C=CC=CC=2)[CH2:14][CH:13]([CH:25]=[CH:26][P:27]([O:32]CC)([O:29]CC)=[O:28])[O:12]1.NC1NC(=O)C2N=NN(C3OC(C=CP(=O)(O)O)CC3O)C=2N=1>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:12][CH:13]([CH:25]=[CH:26][P:27](=[O:28])([OH:29])[OH:32])[CH2:14][CH:15]1[OH:16]

Participants

3

Reactant 2

HCID 72247311Benzoic acid 2-(6-amino-purin-9-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl esterHCID 136381448{2-[5-(5-Amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acid

Product 1

HCID 68593528{2-[5-(6-Amino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acidYield 76.8%

Procedure

Compound 12.2 (103 mg, 68% yield) was synthesized from compound 12.1 (200 mg, 0.41 mmol) using the procedure for the preparation of compound 10.2. 1H NMR (D2O) δ 2.10 (m, 1H), 2.19 (m, 1H), 4.62 (m, 1H), 4.87 (m, 1H), 5.95 (m, 2H), 6.16 (m, 1H), 8.03 (s, 1H), 8.09 (s, 1H). 31P NMR (D2O) d 10.07. LRMS (ESI) MH+ C11H14N5O5P requires 328.2. Found 328.0.

Sources & evidence

ORD record
ord-ef6b3c1c129b473dbbfbea3d43617d10
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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