Dimethyl Sulfoxide → HCID 69912925, compound

HRID 1883558Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]3[O:22][N:21]=[C:20]([CH2:23][CH3:24])[CH:19]=3)[O:12]2)=[C:4]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[N:3]=1.[CH:31]1([NH2:36])[CH2:35][CH2:34][CH2:33][CH2:32]1.CS(C)=[O:39]>>[CH:18]([OH:22])=[O:39].[CH:31]1([NH:36][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[C@H:11]3[C@H:15]([OH:16])[C@H:14]([OH:17])[C@@H:13]([C:18]4[O:22][N:21]=[C:20]([CH2:23][CH3:24])[CH:19]=4)[O:12]3)=[C:4]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[N:3]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 2906Cyclopentylamine

HCID 11212762(2R,3R,4S,5S)-2-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-ethyl-isoxazol-5yl)-tetrahydro-furan-3,4-diol

Product 1

HCID 69912925HCID 69912925, compound

Conditions

Temperature: 90 °C

Procedure

Intermediate 14 (0.206 g, 0.471 mmol) was dissolved in dry DMSO (2.2 ml). An a aliquot of this solution (0.1 ml, 0.021 mmol) was added to cyclopentylamine (0.011 g, 0.126 mmol) in a 1 ml sealed vial (e.g. Reacti-vial™). Mixture was heated at 90° C. for 114.75 h. The resultant crude product was purified by autoprep. HPLC to afford the title compound after freeze-drying as a white solid (0.001 g). LC/MS SYSTEM B Rt=3.07 mins, m/z=486 MH+.

Workup

customsealed vial (e.g. Reacti-vial™)
customThe resultant crude product was purified by autoprep

Sources & evidence

ORD record: ord-79df4605175046b490957dc8cd396322
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762170B1

Reaction notes

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