Triethylamine → Quinazoline

HRID 717212Notes

Reaction equation

HRID 717212 reaction equation
COCCO[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1OCCOC)[N:12]=[CH:11][N:10]=[C:9]2Cl.OC1ON=C(C2C=CC=CC=2)C=1.C(N(CC)CC)C>C(O)(C)C>[N:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:15][CH:14]=2)[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112899424-Chloro-6,7-bis(2-methoxyethoxy)quinazolineHCID 178515567HCID 178515567, compound

Product 1

HCID 9210Quinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

0.3 g (1 mmol) of (6,7-bis(2-methoxyethoxy))-4-chloro-quinazoline was dissolved in 5 mL dry isopropanol. Under stirring, a solution of 0.175 g (1 mmol) of 5-hydroxy3-phenyl-isoxazole in 5 mL of isopropanol was slowly added dropwise to the reaction system, followed by the addition 0.101 g (1 mmol) of freshly distilled triethylamine. After the system was stirred at room temperature for 30 min, the reaction was hold at 60. After the completion of the reaction monitored by TLC, the reaction solution was concentrated under vacuum. The residue was directly separated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give the target compound of (6,7-bis(2-methoxyethoxy))-4-((3-(4-methylphenyl)-isoxazol-5-yl))-methoxy-)-quinazoline (i.e. Q-15 in the following Table). The other compounds were synthesized according to the synthetic process of (6,7-bis(2-methoxyethoxy))-4-((3-(4-methylphenyl)-isoxazol-5-yl))-methoxy-)-quinazoline. The structures were characterized by analytic methods such as IR, 1H NMR, ESI-MS, etc. The physical constants and spectral data of preferred compounds were indicated in the form of table.

Workup

  1. stirringAfter the system was stirred at room temperature for 30 min
  2. concentrationthe reaction solution was concentrated under vacuum
  3. customThe residue was directly separated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-ca8d51e99dc14f3f9c5850f7b6798358
Source dataset
uspto-grants-2015_11
Patent number
US09193718B2

Reaction notes

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