Pyridine → HCID 86758651, compound

HRID 2297659Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([C:21]([OH:23])=O)[O:12]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:37][NH:38][O:39][CH3:40].N1C=CC=CC=1>ClCCl>[CH3:40][O:39][N:38]([CH3:37])[C:21]([C@@H:13]1[C@@H:14]2[C@@H:15]([O:16][C:17]([CH3:20])([CH3:19])[O:18]2)[C@H:11]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[Cl:1])[O:12]1)=[O:23]

Participants

Conditions

Temperature: 22 °C

Procedure

(3aS,4S,6R,6aR)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (35.88 g) was dissolved in dichloromethane (300 ml) and treated with 1,1′-carbonyldiimidazole (20.5 g) with ice-cooling. The solution was stirred at 22° C. for 1 h, N,O-dimethylhydroxylamine hydrochloride (12.3 g) and pyridine (15 ml) were added, and stirring was continued at 22° C. for 24 h. The solution was washed with 0.5M citric acid (250 ml) and 8% sodium bicarbonate (200 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography over silica gel, eluting with ethyl acetate to afford the title compound as a colourless solid (26.4 g).

Workup

temperaturecooling
stirringstirring
waitwas continued at 22° C. for 24 h
washThe solution was washed with 0.5M citric acid (250 ml) and 8% sodium bicarbonate (200 ml)
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was purified by flash chromatography over silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-49fe92590fbb4becadf7bff485d48002
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492348B1

Reaction notes

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