Triethylamine → HCID 10254259, compound

HRID 1793796Notes

Reaction equation

HRID 1793796 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[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([C:23]#[CH:24])[O:17]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([F:35])([F:34])[F:33].C(N(CC)CC)C>O1CCCC1.[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]([C:23]#[C:24][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[O:17]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 10131507HCID 10131507, compound2×

Product 1

HCID 10254259HCID 10254259, compound

Reagents, catalysts & solvents 2

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

Procedure

To a solution of (4S,2R,3R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-ethynyloxolane-3,4-diol (40 mg, 0.12 mmol) in tetrahydrofuran (4 mL) under nitrogen was added catalytic amounts (3 mg) of (4S,2R,3R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-ethynyloxolane-3,4-diol (II) and copper (I) iodide, followed by 1-iodo-2-trifluoromethylbenzene (0.042 mL). Triethylamine (0.4 mL) was then added, and the mixture was stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC, eluting with methanol:methylene chloride (6.5:1), to yield (4S,2R,3R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-{2-[2-(trifluoromethyl)phenyl]ethynyl}-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 TLC
  3. washeluting with methanol:methylene chloride (6.5:1)

Sources & evidence

ORD record
ord-d2a0f5cfdcd44dc9883f896fcc688efa
Source dataset
uspto-grants-2006_04
Patent number
US07022681B2

Reaction notes

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