Ethanol → HCID 22663125, compound

HRID 275740Notes

Reaction equation

HRID 275740 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([NH:15][CH3:16])[N:7]=[C:6]2[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1.C(N(CC)CC)C.C(O)C.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([NH:15][CH3:16])[N:7]=[C:6]2[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 12150252HCID 12150252, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22663125HCID 22663125, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

70.0 mg of 6,7-dimethoxy-2-methylamino-4-[3-(2-phenyl ethynyl)phenyl]quinazoline obtained in Example 65, 50.0 mg Lindlar catalyst and 50.0 mg triethylamine were suspended in a mixed solvent of 5 ml ethanol and 5 ml tetrahydrofuran. After the atmosphere was replaced with hydrogen, the mixture was stirred for 6 hours at ordinary pressure at room temperature. The reaction solution was filtered, and the filtrate was evaporated. Then, the crude product was purified and separated by silica gel column chromatography (hexane: ethyl acetate=2:1). The product was recrystallized from hexane-isopropanol to give 45.0 mg of the title compound as colorless crystals. m.p.; 95-97° C. MASS 400 (MH+)

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe filtrate was evaporated
  3. customThen, the crude product was purified
  4. customseparated by silica gel column chromatography (hexane: ethyl acetate=2:1)
  5. customThe product was recrystallized from hexane-isopropanol

Sources & evidence

ORD record
ord-59f10709792f407cb0c1cbd272a3246b
Source dataset
uspto-grants-2002_03
Patent number
US06352989B1

Reaction notes

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