2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 20220996, compound

HRID 980827Notes

Reaction equation

HRID 980827 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[O:17]=[C:18]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:19]1>C(O)CC(C)C>[OH2:13].[OH2:17].[ClH:1].[ClH:1].[NH2:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=[C:2]([N:29]2[CH2:28][CH2:27][N:26]([C:20]3[CH2:21][C:22]([CH3:24])([CH3:25])[CH2:23][C:18](=[O:17])[CH:19]=3)[CH2:31][CH2:30]2)[N:11]=1.[NH2:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=[C:2]([N:29]2[CH2:28][CH2:27][N:26]([C:20]3[CH2:21][C:22]([CH3:24])([CH3:25])[CH2:23][C:18](=[O:17])[CH:19]=3)[CH2:31][CH2:30]2)[N:11]=1

Participants

5

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 648131HCID 648131, compound

Product 2

HCID 13520910HCID 13520910, compoundYield 78%HCID 20220996HCID 20220996, compoundYield 204.6%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 4.8 g (0.02 mol) of 2-chloro-4-amino-6,7-dimethoxyquinazoline, 4.6 g (0.022 mol) of (3-oxo-5,5-dimethyl-1-cyclohexen-1-yl)-piperazine and 80 ml of isoamyl alcohol is boiled under reflux for 3 hours, with stirring. During the reaction time, the monohydrochloride precipitates. The mixture is left to stand overnight and the crystals are filtered off with suction. After washing with 40 ml of isoamyl alcohol and twice with in each case 40 ml of absolute acetone and 40 ml of absolute ether and drying, 7.1 g of the hydrochloride of 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-4-(3-oxo-5,5-dimethyl-1-cyclohexen-1-yl)-piperazine (78% yield) of melting point 267°-268° C. (decomposition) are obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. customDuring the reaction time, the monohydrochloride precipitates
  3. waitThe mixture is left
  4. filtrationthe crystals are filtered off with suction
  5. washAfter washing with 40 ml of isoamyl alcohol and twice with in each case 40 ml of absolute acetone and 40 ml of absolute ether
  6. customdrying

Sources & evidence

ORD record
ord-1e60c489c4ba42d28fff569f6bbcc569
Source dataset
uspto-grants-1987_01
Patent number
US04639453

Reaction notes

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