Tetrahydrofuran → 4-Amino-6,7-dimethoxy-2-[4-(2-pentenoyl)-1-piperazinyl]-quinazoline

HRID 2295737Notes

Reaction equation

HRID 2295737 reaction equation
O1CCCC1.Cl.[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[C:10]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:9]=1.[C:28](Cl)(=[O:33])[CH:29]=[CH:30][CH2:31][CH3:32]>C(N(CC)CC)C>[NH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[C:10]([N:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:33])[CH:29]=[CH:30][CH2:31][CH3:32])[CH2:24][CH2:23]2)[N:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2760310HCID 2760310, compoundHCID 204738332-Piperazine-4-amino-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 545194944-Amino-6,7-dimethoxy-2-[4-(2-pentenoyl)-1-piperazinyl]-quinazolineYield 50.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 20 ml of tetrahydrofuran were added 2.4 g of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline hydrochloride and 2.6 of triethylamine, after which the mixture was stirred for 20 minutes. There was then added 0.78 g of 2-pentenoyl chloride, after which the mixture was stirred at room temperature for 15 hours. The resulting crystals were collected by filtration, washed with water and recrystallized from ethanol, to give 1.23 g of the desired Compound No. 5 in the form of pale brown needles melting at 246°-247° C.

Workup

  1. stirringafter which the mixture was stirred at room temperature for 15 hours
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6d7ef498ce714f46b4899d87fa3e9678
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

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