Ammonia → 4-Amino-2-chloro-5-cyclobutyloxy-6,7-dimethoxyquinazoline

HRID 2228502Notes

Reaction equation

HRID 2228502 reaction equation
[CH:1]1([O:5][C:6]2[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]3[C:7]=2[C:8](Cl)=[N:9][C:10]([Cl:20])=[N:11]3)[CH2:4][CH2:3][CH2:2]1.[NH3:22]>>[NH2:22][C:8]1[C:7]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[C:15]([O:16][CH3:17])[C:6]=2[O:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[N:11]=[C:10]([Cl:20])[N:9]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 184706425-Cyclobutyloxy-2,4-dichloro-6,7-dimethoxyquinazoline

Product 1

HCID 184706574-Amino-2-chloro-5-cyclobutyloxy-6,7-dimethoxyquinazolineYield 68%

Procedure

5-Cyclobutyloxy-2,4-dichloro-6,7-dimethoxyquinazoline (300 mg, 0.0009 mol) was suspended in a saturated ethanolic ammonia solution (10 ml) and the reaction stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, resuspended in a minimum volume of diethyl ether and the resulting solid filtered off. Drying under suction gave the subtitle compound as a white solid (189 mg, 68%). Rf 0.69 (diethyl ether). 1H-NMR (CDCl3): Γ=1.56 (1H, m), 1.82 (1H, m), 2.26 (2H, m), 2.42 (2H, m), 3.85 (3H, s), 3.94 (3H, s), 4.92 (1H, m), 5.82 (1H, bs), 6.94 (1H, s), 7.72 (1H, bs).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe resulting solid filtered off
  3. customDrying under suction

Sources & evidence

ORD record
ord-f56dea8e9c17456d8f8d55c7bcd2a2e3
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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