Dimethyl Sulfoxide → (2S,3S,4R,5R)-2-(3-Ethyl-[1,2,4]oxadiazol-5-yl)-5-(6-(1-ethyl-propylamino)-2-[2-(1-methyl-1H-imidazol-4-yl)-ethylamino]-purin-9-yl}tetrahydro-furan-3,4-diol formate

HRID 397981Notes

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.[CH3:31][N:32]1[CH:36]=[C:35]([CH2:37][CH2:38][NH2:39])[N:34]=[CH:33]1.CS(C)=[O:42]>>[CH:18]([OH:22])=[O:42].[CH2:23]([C:20]1[N:19]=[C:18]([C@@H:13]2[C@@H:14]([OH:17])[C@@H:15]([OH:16])[C@H:11]([N:8]3[CH:7]=[N:6][C:5]4[C:9]3=[N:10][C:2]([NH:39][CH2:38][CH2:37][C:35]3[N:34]=[CH:33][N:32]([CH3:31])[CH:36]=3)=[N:3][C:4]=4[NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[O:12]2)[O:22][N:21]=1)[CH3:24]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 36141-Methylhistamine2×

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 70020463(2S,3S,4R,5R)-2-(3-Ethyl-[1,2,4]oxadiazol-5-yl)-5-(6-(1-ethyl-propylamino)-2-[2-(1-methyl-1H-imidazol-4-yl)-ethylamino]-purin-9-yl}tetrahydro-furan-3,4-diol formate

Conditions

Temperature: 92.5 °C

Procedure

Intermediate 9 (0.070 g, 0.161 mmol) and 2-(1-methyl-1H-imidazol-4-yl)ethylamine (0.101 g, 0.807 mmol) were dissolved in DMSO (0.03 ml) and heated at 85-100° C. under nitrogen for 8 days, a further portion of 2-(1-methyl-1H-imidazol-4-yl)ethylamine (0.101 g, 0.807 mmol) was added after the first 5 days. The product was purified by Autoprep. HPLC to give the title compound after freeze drying as a cream solid (0.010 g). LC/MS system A Rt=3.36 min, m/z=526 MH+.

Workup

customThe product was purified by Autoprep

Sources & evidence

ORD record: ord-34d6f7ebeb87493e9b38bbb5999c2276
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610665B1

Reaction notes

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