Triethylamine → HCID 58618547, compound

HRID 1793795Notes

Reaction equation

HRID 1793795 reaction equation
[C:1]([C@@H:3]1[C@@H:10]2[C@@H:6]([O:7][C:8]([CH3:12])([CH3:11])[O:9]2)[C@H:5]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[O:4]1)#[CH:2].I[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([F:38])([F:37])[F:36].C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[CH3:11][C:8]1([CH3:12])[O:7][C@@H:6]2[C@@H:10]([C@@H:3]([C:1]#[C:2][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]([F:38])([F:37])[F:36])[O:4][C@H:5]2[N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[O:9]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 58618539HCID 58618539, compound

Product 1

HCID 58618547HCID 58618547, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [9-((1R,2R,4R,5R)-4-ethynyl-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine (40 mg, 0.12 mmol), a compound of formula (5), in tetrahydrofuran (4 ml) under nitrogen was added catalytic amounts (3 mg) of dichlorobis(triphenylphosphine)palladium(II) and copper(II)iodide, followed by 1-iodo-2-trifluoromethylbenzene (0.25 ml, 0.3 mmol). Triethylamine (0.4 ml) was then added, and the mixture 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 [9-((1R,2R,4R,5R)-7,7-dimethyl-4-{2-[2-(trifluoromethyl)-phenyl]ethynyl}-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine, a compound of formula (6).

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-1518cf6339854ca9831a3ed3ec3e5a15
Source dataset
uspto-grants-2006_04
Patent number
US07022681B2

Reaction notes

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