(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → N-[4-(benzyloxy)phenyl]-6-(1-methyl-1H-imidazol-5-yl)quinazolin-4-amine

HRID 2306712Notes

Reaction equation

HRID 2306712 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](Br)[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.[CH3:27][N:28]1[C:32]([Sn](CCCC)(CCCC)CCCC)=[CH:31][N:30]=[CH:29]1>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]([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:32]4[N:28]([CH3:27])[CH:29]=[N:30][CH:31]=4)[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

5

Reactant 2

HCID 1569266(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amineHCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazole

Product 1

HCID 22609863N-[4-(benzyloxy)phenyl]-6-(1-methyl-1H-imidazol-5-yl)quinazolin-4-amineYield 90%

Reagents, catalysts & solvents 2

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

Procedure

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (1.0 g, 2.46 mmol), 1-methyl-5-(tributylstannyl)imidazole (prepared according to Gaare, K., et al. Acta Chem. Scand. (1993), 47(1), 57-62) (1.25 g, 3.37 mmol) and bis(triphenylphosphine)palladium (II) chloride (catalytic amount) were reacted according to Procedure B in dioxane (50 ml) for 3 hours. The solvent was removed in vacuo, and the solid was washed with i-hexane. The resulting dark solid was suspended in IMS, and undissolved material removed by filtration. The resulting filtrate was concentrated in vacuo to give the product as a pale baige solid (0.90 g, 2.21 mmol, 90%); δH [2H6]-DMSO 9.69 (1H, b, NH), 8.60 (1H, s, 5-H), 8.55 (1H, s, 2-H), 8.00 (1H, d, 7-H), 7.83 (2H, m, 8-H, imidazole-H), 7.69 (2H, d, 2′-H, 6′-H), 7.52-7.33 (5H, m, 5×Ph-H), 7.22 (1H, s, imidazole-H), 7.09 (2H, d, 3′-H, 5′-H), 5.14 (2H, s, CH2), 3.80 (3H, s, CH3); m/z 408 (M+1)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washthe solid was washed with i-hexane
  3. customundissolved material removed by filtration
  4. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1c4cc2c64b904966a69dc2b15866fb6d
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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