Potassium Carbonate → 6-Methoxy-4-phenoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline

HRID 1597220Notes

Reaction equation

Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[OH:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:29][O:28][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:11]=1[O:10][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)[N:18]=[CH:17][N:16]=[C:15]2[O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(2-Chloroethyl)pyrrolidine hydrochloride (1.27 g, 7.5 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (1.0 g, 3.7 mmol), and potassium carbonate (3.9 g, 28.3 mmol) in DMF (30 ml). The mixture was heated at 110° C. for 4 hours and allowed to cool. The mixture was filtered, and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol/ammonia, (100/8/1) to give an oil which was triturated with ethyl acetate to give 6-methoxy-4-phenoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline (200 mg, 15%) as a white solid.

Workup

temperatureto cool
filtrationThe mixture was filtered
customthe volatiles were removed from the filtrate by evaporation
customThe residue was purified by column chromatography
washeluting with methylene chloride/methanol/ammonia, (100/8/1)
customto give an oil which
customwas triturated with ethyl acetate

Sources & evidence

ORD record: ord-7effe967a9a744359d801c5feeca77b2
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294532B1

Reaction notes

Loading…