2-Chloroadenosine → HCID 24944879, compound

HRID 1157425Notes

Reaction equation

HRID 1157425 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[Cl:21][C:22]1[CH:23]=[C:24]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:25]=[CH:26][C:27]=1[Cl:28]>C1COCC1>[NH2:20][C:4]1[N:3]=[C:2]([N:32]2[CH2:31][CH2:30][N:29]([C:24]3[CH:25]=[CH:26][C:27]([Cl:28])=[C:22]([Cl:21])[CH:23]=3)[CH2:34][CH2:33]2)[N:19]=[C:18]2[C:5]=1[N:6]=[CH:7][N:8]2[C@H:9]1[C@H:10]([OH:11])[C@H:12]([OH:13])[C@@H:14]([CH2:15][OH:16])[O:17]1

Participants

4

Reactant 2

HCID 89742-ChloroadenosineHCID 936011-(3,4-Dichlorophenyl)piperazine

Product 1

HCID 24944879HCID 24944879, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-chloro adenosine (80 mg, 0.27 mmol) in THF (4 mL) was added 4-(3,4-dichlorophenyl)piperazine (122 mg, 0.53 mmol) and the resulting solution heated in a Biotage microwave (150° C., absorption high, pre-stirring 30 s) for 30 min. The solvents were then removed in vacuo and the residue purified twice by reverse phase prep HPLC (Phenomenex Synergi, RP-Hydro 150×10 mm, 10μ, 20 mL per min, gradient 5-100% acetonitrile in water over 18 min, product eluted in 80% acetonitrile) and (Phenomenex Synergi, RP-Hydro 150×10 mm, 10μ, 20 mL per min, gradient 5-100% acetonitrile in water over 9 min, product eluted in 55% acetonitrile) to yield (2R,3R,4S,5R)-2-(6-amino-2-(4-(3,4-dichlorophenyl)piperazin-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 8 as a white solid (7.9 mg, 6%)

Workup

  1. customThe solvents were then removed in vacuo
  2. customthe residue purified twice by reverse phase prep HPLC (Phenomenex Synergi, RP-Hydro 150×10 mm, 10μ, 20 mL per min, gradient 5-100% acetonitrile in water over 18 min, product eluted in 80% acetonitrile) and (Phenomenex Synergi, RP-Hydro 150×10 mm, 10μ, 20 mL per min, gradient 5-100% acetonitrile in water over 9 min, product eluted in 55% acetonitrile)

Sources & evidence

ORD record
ord-c79b42b0b362471f9f7af78d9d73c668
Source dataset
uspto-grants-2010_10
Patent number
US07807685B2

Reaction notes

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