(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → HCID 22609718, compound

HRID 1936782Notes

Reaction equation

HRID 1936782 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.C([Sn](CCCC)(CCCC)[C:32]1[N:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=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:32]4[N:37]=[CH:36][CH:35]=[CH:34][N:33]=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 27632512-(Tributylstannyl)pyrimidine

Product 1

HCID 22609718HCID 22609718, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)amine (200 mg, 0.49 mmol), 2-(tributylstannyl)pyrimidine (200 mg, 0.54 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (3 ml) and heated at reflux under nitrogen for 27 hr (Procedure B). The solvent was removed from the cooled reaction under vacuum, and the residue was purified by flash column chromatography (silica gel, eluting with an ethyl acetate/iso-hexane gradient). The resulting oily solid was triturated with iso-hexane/ethyl acetate to give the product (80 mg, 40%) as a pale yellow solid; δH [2H6]-DMSO 10.30 (1H, b, NH), 9.61 (1H, s, 5-H), 9.07 (2H, d, pyrimidine 4-H, pyrimidine 6-H), 8.86 (1H, d, 7-H), 8.51 (1H, s, 2-H), 7.93 (1H, d, 8-H), 7.78 (2H, d, 2′-H, 6′-H), 7.65-7.36 (6H, m, 5×Ph-H, pyrimidine 5-H), 7.11 (2H, d, 3′-H, 5′-H), 5.18 (2H, s, CH2); m/z 406 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 27 hr (Procedure B)
  3. customThe solvent was removed from the cooled reaction under vacuum
  4. customthe residue was purified by flash column chromatography (silica gel
  5. washeluting with an ethyl acetate/iso-hexane gradient)
  6. customThe resulting oily solid was triturated with iso-hexane/ethyl acetate

Sources & evidence

ORD record
ord-18b10592eb494a10a67ad34509983869
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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