Hydrogen Bromide → HCID 53974663, compound

HRID 128570Notes

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[C:11]([C:13]([F:37])([F:36])[C@@:14](O[Si](C(C)(C)C)(C)C)([C@@H:16]([CH:18](O[Si](C(C)(C)C)(C)C)[OH:19])[OH:17])[OH:15])=[O:12].Br>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C:11]([C:13]([F:37])([F:36])[C@@H:14]([C@@H:16]([CH2:18][OH:19])[OH:17])[OH:15])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 100 mg (0.194 mmol) of 1-(6-amino-9H-purin-9-yl)-3,5-bis(t-butyldimethylsiloxy)-2-desoxy-2,2-difluororibose dissolved in 25 ml of methylene chloride cooled to about 0° C. with an external ice bath was saturated with anhydrous hydrogen bromide gas. The mixture was stirred at about 0° C. for about 4 hours, and nitrogen was bubbled through the reaction mixture. The mixture was filtered and the collected solid was washed with methanol to provide 110 mg of solid. The solid was purified by HPLC to provide 12.1 mg of β-1-(6-amino-9H-purin-9-yl)-2-desoxy-2,2-difluororibose and 6.3 mg of α-1-(6-amino-9H-purin-9-yl)-2-desoxy-2,2-difluororibose.

Workup

customnitrogen was bubbled through the reaction mixture
filtrationThe mixture was filtered
washthe collected solid was washed with methanol

Sources & evidence

ORD record: ord-c6cc241c8007482d95debc95a161ecc8
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464826

Reaction notes

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