Triethylamine → (4-Benzyloxy-phenyl)-(6-(3-methyl-[1,2]oxazol-4-yl)-quinazolin-4-yl)-amine

HRID 2306754Notes

Reaction equation

HRID 2306754 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24](I)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Sn](CCCC)(CCCC)[C:33]1[C:34]([CH3:38])=[N:35][O:36][CH:37]=1)CCC.C(N(CC)CC)C>O1CCOCC1.[Ag]=O>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:33]4[C:34]([CH3:38])=[N:35][O:36][CH:37]=4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108940213-Methyl-4-(tributylstannyl)isoxazoleHCID 21951949(4-Benzyloxyphenyl)-(6-iodoquinazolin-4-yl)-amine Hydrochloride

Product 1

HCID 22609816(4-Benzyloxy-phenyl)-(6-(3-methyl-[1,2]oxazol-4-yl)-quinazolin-4-yl)-amine

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine hydrochloride (0.35 g) in dioxan (10 ml) under nitrogen was treated with 4-tributylstannyl-3-methylisoxazole (prepapred according to the literature method: Heterocycles, (1996), 43(6), 1301-1304) (0.4 g), silver oxide (0.092 g), triethylamine (0.1 ml) and [1.4-bis(diphenylphosphino)butane]palladium (II) chloride (0.1 g) at 90° C. for 16 hours. The mixture was cooled, adsorbed onto silica and purified by chromatography. Trituration from hexane and filtration gave the title compound (0.20 g); δH [2H6]DMSO 9.78(1H, bs), 9.22(1H, s), 8.57(1H, s), 8.53(1H, s), 7.98(1H, d), 7.83(1H, d), 7.67(2H, d), 7.42(5H, m), 7.09(1H, d), 5.64(2H, s) 2.51 (3H, s); m/z (M+1)+ 409.

Workup

  1. temperatureThe mixture was cooled
  2. custompurified by chromatography
  3. filtrationTrituration from hexane and filtration

Sources & evidence

ORD record
ord-dc3a0254e11047599f1834f3622abb5d
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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