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

HRID 1826267
Notes
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Reaction equation

HRID 1826267 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-404df7edad6042cb92c7b16716580c16
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07049438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes