2-(Tributylstannyl)furan → (1-Benzyl-1H-indazol-5-yl)-(pyrido[3,4-d]pyrimidin-4-yl)-amine

HRID 2085948Notes

Reaction equation

HRID 2085948 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[CH:26][N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 21952012(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine

Product 1

HCID 22727452(1-Benzyl-1H-indazol-5-yl)-(pyrido[3,4-d]pyrimidin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of (1-Benzyl-1H-indazol-5-yl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (0.165 g), 2-(tri-n-butylstannyl)furan (0.139 g) and bis-(triphenylphosphine)palladium (II) chloride (30 mg) in dioxane (10 ml) was heated at reflux under nitrogen for 65 hr (Procedure B). The cooled mixture was absorbed onto silica and chromatographed to give the title compound as an orange solid; δH CDCl3 9.34(1H,s), 8.82(1H,s), 8.70(1H,d), 8.15(1H,d), 8.10(1H,s), 7.65(1H,d), 7.60(1H,s), 7.53(1H,dd), 7.40(1H,d), 7.25(6H,m), 5.60(2H,s); m/z (M+1)+353.

Workup

  1. temperatureat reflux under nitrogen for 65 hr (Procedure B)
  2. customThe cooled mixture was absorbed onto silica
  3. customchromatographed

Sources & evidence

ORD record
ord-e59afd2561f042e59e757034c1f2ec2e
Source dataset
uspto-grants-2004_04
Patent number
US06723726B1

Reaction notes

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