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

HRID 2295734Notes

Reaction equation

HRID 2295734 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.[CH3:28][C:29](=[CH2:33])[C:30](Cl)=[O:31]>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:30](=[O:31])[C:29]([CH3:33])=[CH2:28])[CH2:24][CH2:23]2)[N:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 13528Methacryloyl chlorideHCID 204738332-Piperazine-4-amino-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 128370984-Amino-6,7-dimethoxy-2-[4-(2-methylacryloyl)-1-piperazinyl]quinazolineYield 39%

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 g of triethylamine, after which the mixture was stirred for 30 minutes. There was then added 0.6 g of 2-methylacryloyl chloride, after which the mixture was stirred at room temperature for 8 hours. The crystals which were produced were collected by filtration, washed with water and recrystallized from ethanol to give 0.8 g of the desired Compound No. 2 in the form of colourless needles melting at 262°-263° C. (with decomposition).

Workup

  1. stirringafter which the mixture was stirred at room temperature for 8 hours
  2. customThe crystals which were produced
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-114bbfd9999b4caeb66de7fe486fa3fe
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

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