O-Methylhydroxylamine → 1-(2'-C-methyl-beta-D-ribofuranosyl)-4-methoxylamino-pyrazolo[3,4-d]pyrimidine

Reaction equation

[CH3:1][C@@:2]1([OH:21])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2=[N:15][CH:16]=[N:17][C:18]([NH:19][OH:20])=[C:13]2[CH:12]=[N:11]1.O(N)[CH3:23]>>[CH3:1][C@@:2]1([OH:21])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2=[N:15][CH:16]=[N:17][C:18]([NH:19][O:20][CH3:23])=[C:13]2[CH:12]=[N:11]1

Participants

Reactant 2

HCID 4113O-Methylhydroxylamine

HCID 104698851-(2'-C-methyl-beta-D-ribofuranosyl)-4-hydroxylamino-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 104481561-(2'-C-methyl-beta-D-ribofuranosyl)-4-methoxylamino-pyrazolo[3,4-d]pyrimidine

Procedure

Nucleoside 119 was prepared from the nucleoside 143 (Example 6, step 3) substituting hydroxylamine for methoxylamine.

Sources & evidence

ORD record: ord-63a38c226fc942f48e15721c8dc0e18a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425547B2

Reaction notes

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