반응 #167468

반응 방정식

p-anisidine

Anthranilic acid

3-phthalimidopropionic acid

triphenylphosphite

→

2-{2-[3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione

용매

pyridine

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   온도heating at 100° C.
3. 3
   기타The pyridine was removed
4. 4
   기타by azeotroping with toluene
5. 5
   기타The solids that crashed out were removed
6. 6
   기타the residue was purified by silica gel chromatography with gradient elution (0 to 100% EtOAc in hexanes)
7. 7
   기타A white solid precipitated from several of the fractions which
8. 8
   기타was isolated by filtration
9. 9
   기타to provide A-1 (2.23 g, 36%)

실험 절차

Anthranilic acid (2.0 g, 14.6 mmol), 3-phthalimidopropionic acid (3.2 g, 14.6 mmol), and triphenylphosphite (4.0 mL, 15.3 mmol) were dissolved in pyridine (20 mL) and heated in a sealed tube at 100° C. for 2 hours. After cooling to room temperature, the tube was opened, p-anisidine (2.7 g, 21.9 mmol) was added and heating at 100° C. was resumed for 4 hours. The pyridine was removed by azeotroping with toluene, and the residue was suspended in CHCl3 and toluene. The solids that crashed out were removed, and the residue was purified by silica gel chromatography with gradient elution (0 to 100% EtOAc in hexanes). A white solid precipitated from several of the fractions which was isolated by filtration to provide A-1 (2.23 g, 36%). Data for A-1: LRMS: calculated M+H for C25H19N3O4: 426.14. Found: 426.16.

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