Cesium carbonate → (+/-)-Trans-5-(2'-Amino-6'-Chloropurin-9-ylmethyl)-2-Diethoxyphosphinoyl-Tetrahydrofuran

HRID 618849Notes

Reaction equation

Br[CH2:2][C@@H:3]1[O:7][C@@H:6]([P:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4]1.[NH2:16][C:17]1[N:25]=[C:24]2[C:20]([NH:21][CH:22]=[N:23]2)=[C:19]([Cl:26])[N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH2:16][C:17]1[N:25]=[C:24]2[C:20]([N:21]=[CH:22][N:23]2[CH2:2][C@@H:3]2[O:7][C@@H:6]([P:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4]2)=[C:19]([Cl:26])[N:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (±)-trans-5-bromomethyl-2-diethoxyphosphinoyl-tetrahydrofuran (example 66) (529 mg, 1.76 mmol), 2-amino-6-chloropurine (358 mg, 2.11 mmol) and cesium carbonate (860 mg, 2.64 mmol) in dry DMF (2 mL) was stirred at 90° C. for 6 h. The mixture was then cooled and filtered. Concentration of the filtrate gave a residue which was purified by chromatography eluting with 2→5% MeOH in methylene chloride. The desired product was obtained a foam (384 mg, 56%).

Workup

temperatureThe mixture was then cooled
filtrationfiltered
customConcentration of the filtrate gave a residue which
customwas purified by chromatography
washeluting with 2→5% MeOH in methylene chloride

Sources & evidence

ORD record: ord-30e272e6776443c2aa540ca3a40c3511
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05955610

Reaction notes

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