Isopropanol → 6,7-Dimethoxy-2-(2-pyridinyl)-4-quinazolinamine

HRID 1576330Notes

Reaction equation

HRID 1576330 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[N:21].C[O-].[Na+].C(O)(C)C>O>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=2)[N:1]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[N:21]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7522Pyridine-2-carbonitrileHCID 7359672-Amino-4,5-dimethoxybenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 215119446,7-Dimethoxy-2-(2-pyridinyl)-4-quinazolinamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.9 g. (0.05 mol) of 6-aminoveratronitrile, 5.2 g. (0.05 mol) of 2-pyridine carbonitrile and 5.4 g. (0.1 mol) of sodium methoxide in 250 ml. of isopropanol are refluxed for 48 hours under a nitrogen atmosphere. The reaction mixture is then decomposed with water and the isopropanol is distilled off. 80 ml. of diethyl ether and 80 ml. of water are added and the layers are separated. The water is distilled off from the aqueous layer and the residue is dissolved in 100 ml. of chloroform. The solution is filtered and the chloroform is distilled off. The residue is crystallized from toluene to give 4-amino-6,7-dimethoxy-2-(2-pyridyl)quinazoline, m.p. 248° - 251°C. The base is converted into the monohydrochloride, and the salt after crystallization from a mixture of water and isopropanol, melts above 310°C.

Workup

  1. distillationthe isopropanol is distilled off
  2. additionof water are added
  3. customthe layers are separated
  4. distillationThe water is distilled off from the aqueous layer
  5. dissolutionthe residue is dissolved in 100 ml
  6. filtrationThe solution is filtered
  7. distillationthe chloroform is distilled off
  8. customThe residue is crystallized from toluene

Sources & evidence

ORD record
ord-3c6105c20d27489f8eb1678e3e9c324e
Source dataset
uspto-grants-1976_09
Patent number
US03980650

Reaction notes

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