3-Ethynylaniline hydrochloride → (6-Carbomethoxyquinazolin-4-yl)-(3-ethynylphenyl)-amine Hydrochloride

HRID 1869075

Reaction equation

HRID 1869075 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.Cl.[C:17]([C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22])#[CH:18]>C(O)(C)(C)C.C(O)(C)C>[ClH:1].[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([C:17]#[CH:18])[CH:20]=1)([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 189250233-Ethynylaniline hydrochlorideHCID 18925080Methyl 4-chloroquinazoline-6-carboxylate

Product 1

HCID 18925071(6-Carbomethoxyquinazolin-4-yl)-(3-ethynylphenyl)-amine Hydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6386tert-ButanolSolvent

Procedure

4-Chloro-6-carbomethoxyquinazoline (100 mg, 0.450 mmol) and 3-ethynylaniline hydrochloride (53.4 mg, 0.456 mmol) were refluxed in 2 mL of tert-butyl alcohol for 2 hours, cooled, diluted with 2 mL of isopropyl alcohol and filtered to afford solid title product which was washed with 10 mL of diethyl ether and dried, in vacuo, at 70° C., 122 mg (80%); mp 232°-233° C. (dec).

Workup

  1. temperaturecooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-e3575eab7f0144ebb14c6edee87de436
Source dataset
uspto-grants-2009_12
Patent number
USRE041065E1

Linked notes

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