2-Pyridinamine, 5-iodo- → N-(5-Methoxypyridin-2-yl)-2-methylquinazolin-4-amine

HRID 1876143Notes

Reaction equation

HRID 1876143 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][N:12]=1.C[O-].[Na+]>CO.[Cu]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:13]2[C:14]3[C:15](=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:10]=[C:11]([CH3:16])[N:12]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 885792-Pyridinamine, 5-iodo-HCID 10942334Sodium MethoxideHCID 113209342-Amino-5-methoxypyridine

Product 1

HCID 42625988N-(5-Methoxypyridin-2-yl)-2-methylquinazolin-4-amineYield 31%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
160 °C

Procedure

2-Amino-5-methoxy-pyridine. A mixture of 2-amino-5-iodo-pyridine (1 g, 4.54 mmol) in 20 mL of absolute methanol with 400 mg of copper powder and sodium methoxide (6 mmol) was heated at 160° C. overnight in a seal tube. The reaction mixture was cooled to room temperature, diluted with 80 mL of methanol and filtered through a pad of celite. The filtrate was concentrated and the residue was purified by chromatography (80% ethyl acetate/hexane) to give the title compound (174 mg, 31%). 1H NMR (CDCl3): 7.78 (d, J=2.7, 1H), 7.09 (dd, J=3.0, 9.0, 1H), 6.48 (d, J=9.0, 1H), 3.78 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by chromatography (80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-557a6a390b1248d4a40e0baacbcba354
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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