Triethylamine → HCID 69469249, compound

HRID 1793799Notes

Reaction equation

HRID 1793799 reaction equation
[CH:1]1([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[CH:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][C:24]#[CH:25])[O:17]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1I.CCN(CC)CC>C1COCC1.[Cu]I>[CH:1]1([NH:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][C:24]#[C:25][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[F:26])[O:17]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 676731-Fluoro-2-iodobenzeneHCID 86591276HCID 86591276, compound

Product 1

HCID 69469249HCID 69469249, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of (4S,2R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-prop-2-ynyloxolane-3,4-diol (0.017 g, 0.05 mmol) and 1-fluoro-2-iodobenzene (0.02 mL, 0.13 mmol) in THF (3.50 mL) under an atmosphere of N2 was added catalytic amount of dichlorobis(triphenylphosphine) palladium (II) and copper (I) iodide. Et3N (0.20 mL) was then added. The resulting mixture was stirred under N2 at 75° C. for 2 days. The solvent was removed under reduced pressure, and the residue was purified by preparative thin layer chromatography to give (4S,2R,3R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-[3-(2-fluorophenyl)prop-2-ynyl]oxolane-3,4-diol, a compound of Formula I.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-932b9dc854144230a5c6160a73ab9d8d
Source dataset
uspto-grants-2006_04
Patent number
US07022681B2

Reaction notes

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