Stannanecarbonitrile, tributyl- → (4-Benzyloxy-phenyl)-(6-cyanoquinazolin-4-yl)-amine

HRID 1936760Notes

Reaction equation

HRID 1936760 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23](I)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn]([C:40]#[N:41])(CCCC)CCCC)CCC>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:40]#[N:41])[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 21951950(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine

Product 1

HCID 22609759(4-Benzyloxy-phenyl)-(6-cyanoquinazolin-4-yl)-amineYield 73.8%

Reagents, catalysts & solvents 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine (1.2 g) in dioxane (10 ml) under N2 was treated with tributyltin cyanide (0.79 g) and catalytic quantities of 1,4-bis-(diphenylphosphino)-butane palladium (II) chloride and tetrakis (triphenylphosphine) palladium at reflux for 23 hours. The mixture was absorbed onto silica and chromatographed to give the title compound (0.65 g); δH [2H6]DMSO 10.01(1H,s), 9.14(1H,s), 8.63(1H,s), 8.15(1H,d), 7.87(1H,d), 7.73(2H,d), 7.45(5H,m), 7.10(2H,d), 5.13(2H,s); m/z (M+1)+353.

Workup

  1. temperatureat reflux for 23 hours
  2. customThe mixture was absorbed onto silica
  3. customchromatographed

Sources & evidence

ORD record
ord-3d604d7bcad240a6a662f845e3f1081c
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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