Dimethylformamide → HCID 11208563, compound

HRID 2050600Notes

Reaction equation

I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH3:21][N:22](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])#[N:22]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-iodoadenosine (0.500 g, 1.27 mmol) in DMF (70 mL) was added tetrakis(triphenylphosphine)palladium (0) (0.220 g, 0.19 mmol) and n-tributyltin cyanide (0.442 g, 1.39 mmol). The mixture was stirred at 120° C. for 20 h under nitrogen. The solvent was then evaporated and the residue was purified on silica gel to give 2-cyanoadenosine in 86% yield. 2-Cyanoadenosine was converted to I by using in sequence the following procedures: Procedure A (60% yield), Procedure B (89% yield), Procedure C (60% yield), Procedure D (63% yield), Procedure E (70% yield) and Procedure F (70% yield): mp 195°-197° C.; 13C NMR (Me2SO-d6) 625.4, 32.0, 62.6, 82.3, 84.7, 117.0, 120.7, 136.6, 141.5, 147.9, 156.2; 1H NMR (Me2SO-d6) δ2.06 (m, 2H), 2.39 (m, 2H), 3.56 (m, 2H), 4.13 (m, 1H), 4.92 (m, 1H), 6.24 (m, 1H), 7.90 (br.s, 2H), 8.59 (s, 1H); UV (H2O) λmax 297 nm (ε6470), 266 nm (ε9980), 260 nm (ε9270); FAB HRMS obsd (M+ +H) 261.1069, calcd for C11H12N6O2 261.1099.

Workup

customThe solvent was then evaporated
customthe residue was purified on silica gel

Sources & evidence

ORD record: ord-760c61bb7ced40d8a3b629e7fc9c157c
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013829

Reaction notes

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