Sodium Methoxide → (2-methoxy-quinazolin-4-yl)-(4-methoxyphenyl)-methylamine

HRID 1436258Notes

Reaction equation

HRID 1436258 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:22][O-:23].[Na+]>CO.C(OC(=O)C)C>[CH3:22][O:23][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 11437885(2-methoxy-quinazolin-4-yl)-(4-methoxyphenyl)-methylamineYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2-chloro-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (50 mg, 0.167 mmol) in 2 ml methanol was added sodium methoxide (500 μl, 25% by wt. in methanol). The solution was stirred at 80° C. for 1 h, and it was diluted with 50 ml ethylacetate. The solution was washed with water, dried and concentrated. The product was purified using small silica column and isolated as off white solid (22 mg, 54%). 1H NMR (CDCl3): 7.89 (d, J=8.4 Hz, 1H), 7.53 (ddd, J=8.7, 5.4 and 2.4 Hz, 1H), 7.19-7.14 (m, 2H), 6.99-6.93 (m, 2H), 6.90-6.85 (m, 2H), 4.14 (s, 3H), 3.86 (s, 3H), 3.64 (s, 3H).

Workup

  1. washThe solution was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe product was purified

Sources & evidence

ORD record
ord-eda739899c604789a599091beacb00ff
Source dataset
uspto-grants-2009_11
Patent number
US07618975B2

Reaction notes

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