Triphenylphosphine → HCID 68747790, compound

HRID 1396604Notes

Reaction equation

HRID 1396604 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH3:14])[N:3]=1.[CH:34]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:35]=1.C([Sn](CCCC)(CCCC)C=C)CCC>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH:34]=[CH2:35])=[N:3][C:4]([C@@H:13]([NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]3[C:17]=1[N:18]=[CH:19][N:20]3[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[CH3:14])=[CH:5]2

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 86665021HCID 86665021, compound

Product 1

HCID 68747790HCID 68747790, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (S)—N-(1-(1,8-dichloroisoquinolin-3-yl)ethyl)-9-(4-methoxybenzyl)-9H-purin-6-amine 1 (2.58 g, 5.4 mmol, 1 eq), Pd(OAc)2 (363 mg, 1.62 mmol, 0.3 eq) and PPh3 (846 mg, 3.24 mol, 0.6 eq) in THF (50 mL) at RT, tributyl(vinyl)tin (1.97 g, 5.94 mmol, 1.1 eq) was added and the resulting mixture was stirred at reflux overnight. The mixture was allowed to cool to RT and filtered through silica gel (10 g). The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM) to afford the product (S)—N-(1-(8-chloro-1-vinylisoquinolin-3-yl)ethyl)-9-(4-methoxybenzyl)-9H-purin-6-amine 2.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered through silica gel (10 g)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM)

Sources & evidence

ORD record
ord-48a851901e8241159e47b9b9f61ab120
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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