Tetrahydrofuran → 4-(3-Ethoxycarbonylpropyl)Amino-6,7,8-Trimethoxyquinazoline

HRID 1603524Notes

Reaction equation

HRID 1603524 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.O1CCCC1.Cl[C:24]1[C:33]2[C:28](=[C:29]([O:38][CH3:39])[C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1>CC(O)C>[CH2:9]([O:8][C:6]([CH2:5][CH2:4][CH2:3][NH:2][C:24]1[C:33]2[C:28](=[C:29]([O:38][CH3:39])[C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][N:25]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 1006864-Chloro-6,7,8-trimethoxyquinazolineHCID 126496614-Aminobutyrate ethyl hydrochloride

Product 1

HCID 97984504-(3-Ethoxycarbonylpropyl)Amino-6,7,8-TrimethoxyquinazolineYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.0 g of ethyl 4-aminobutyrate hydrochloride (6.0 mmol), 2 ml of triethylamine, 10 ml of tetrahydrofuran and 10 ml of 2-propanol are added to 0.50 g (2.0 mmol) of 4-chloro-6,7,8-trimethoxyquinazoline, followed by heating under reflux one whole day and night. The reaction liquid is distilled under reduced pressure to remove the solvent. The obtained residue is purified by silica gel column chromatography (ethyl acetate) and then recrystallized from ethyl acetate/hexane. Thus, 0.49 g (yield 72%) of a white crystal is obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux one whole day and night
  3. customThe reaction liquid
  4. distillationis distilled under reduced pressure
  5. customto remove the solvent
  6. customThe obtained residue is purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f89c6bd37f1e46618a85f45d67f39c63
Source dataset
uspto-grants-1999_11
Patent number
US05990117

Reaction notes

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