Dimethyl Sulfoxide → (2r,3r,4s,5s)-2-[2-Cyclopentylamino-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-ethyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol formate

HRID 397988Notes

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])[N: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])[N:19]=4)[O:12]3)=[C:4]([NH:25][CH:26]([CH2:27][CH3:28])[CH2:29][CH3:30])[N:3]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 2906Cyclopentylamine

HCID 56625647(2r,3r,4s,5s)-2-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-ethyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol

Product 1

HCID 70022733(2r,3r,4s,5s)-2-[2-Cyclopentylamino-6-(1-ethyl-propylamino)-purin-9-yl]-5-(3-ethyl-[1,2,4]oxadiazol-5-yl)-tetrahydro-furan-3,4-diol formate

Conditions

Temperature: 80 °C

Procedure

Intermediate 9 (0.070 g, 0.161 mmol) and cyclopentylamine (0.08 ml, 0.807 mmol) were dissolved in DMSO (0.03 ml) and heated at 80° C. in a sealed vial (eg Reacti vial™), for 20 h. The product was purified by Autoprep. HPLC to give the title compound after freeze drying as a cream solid (0.008 g). LC/MS system B Rt=3.01 min, m/z=486 MH+.

Workup

customThe product was purified by Autoprep

Sources & evidence

ORD record: ord-86fab960dc6444e7aed93822e34e8b59
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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