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

HRID 1876096Notes

Reaction equation

HRID 1876096 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-5893bce6dcfb4d0f9744376544feb8ee
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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