HCID 17954255, compound → (4S,2R,3R,5R)-2-[2-chloro-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

HRID 855496Notes

Reaction equation

C([O:4][CH:5]1[CH:9]([O:10]C(=O)C)[CH:8](OCC(=O)C)[O:7][CH:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([Cl:29])=[N:23][C:24]=2Cl)(=O)C.[CH3:30][NH2:31].[CH3:32][OH:33]>>[Cl:29][C:22]1[N:21]=[C:20]2[C:25]([N:26]=[CH:27][N:19]2[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([CH2:32][OH:33])[O:7]2)=[C:24]([NH:31][CH3:30])[N:23]=1

Participants

Reactant 2

HCID 17954255HCID 17954255, compound

HCID 57454252Monomethylamine methanol

Product 1

HCID 11243974(4S,2R,3R,5R)-2-[2-chloro-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Procedure

3,4-diacetyloxy-2-(2,6-dichloropurin-9-yl)-5-(2-oxopropoxy)tetrahydrofuran, the compound of formula (1) (1 mmol), was suspended in a mixture of 1:4 methylamine/MeOH, and the mixture stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue triturated in ether, to afford (4S,2R,3R,5R)-2-[2-chloro-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol, a compound of formula (2) as a white solid.

Workup

customThe solvent was removed under reduced pressure
customthe residue triturated in ether

Sources & evidence

ORD record: ord-5dc3579b1589480cadf6da6d45145334
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262176B2

Reaction notes

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