Ethanol → 4-(2-Chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazoline

HRID 641727Notes

Reaction equation

HRID 641727 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[Cl:28])=[N:14][CH:15]=[N:16]2)=[C:11]([O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:10]=1)C1C=CC=CC=1.C(O)C.C1COCC1.[H][H]>[Pd].CN(C=O)C>[Cl:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[N:16]=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 221408327-Benzyloxy4-(2-chloro-5-methoxyanilino)-5-(3-morpholinopropoxy)quinazolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1358309164-(2-Chloro-5-methoxyanilino)-7-hydroxy-5-(3-morpholinopropoxy)quinazolineYield 29.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-4-(2-chloro-5-methoxyanilino)-5-(3-morpholinopropoxy)quinazoline (0.185 g), 10% palladium on charcoal catalyst (0.018 g), ethanol (2.5 ml), THF (2.5 ml) and DMF (1 ml) was stirred under an atmosphere pressure of hydrogen for 16 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and a saturated methanolic ammonia solution as eluent. There was thus obtained the title compound (0.045 g); NMR Spectrum: (DMSOd6) 2.05 (m, 2H), 2.35 (br s, 4H), 2.45 (t, 2H), 3.55 (t, 4H), 3.8 (s, 3H), 4.42 (t, 2H), 6.7 (d, 2H), 7.45 (d, 1H), 8.3 (s, 1H), 8.45 (s, 1H), 10.05 (s, 1H); Mass Spectrum: M+H+ 445.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography on silica using
  4. additiona 9:1 mixture of methylene chloride

Sources & evidence

ORD record
ord-e7ecbd9558c64f79810f95b8a9e8ff9b
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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