Potassium Carbonate → HCID 18474787, compound

HRID 547165Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[Cl:9][C:10]1[CH:29]=[CH:28][C:13]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([OH:27])=[C:22](OC)[CH:23]=3)[N:18]=[CH:17][N:16]=2)=[C:12]([F:30])[CH:11]=1.[C:31](=O)([O-])[O-:32].[K+].[K+]>CN(C=O)C>[Cl:9][C:10]1[CH:29]=[CH:28][C:13]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH2:31][O:32][CH2:2][CH2:3][CH:4]4[O:8][CH2:7][CH2:6][O:5]4)=[CH:22][CH:23]=3)[N:18]=[CH:17][N:16]=2)=[C:12]([F:30])[CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-(2-bromoethyl)-1,3-dioxolane (258 mg, 1.4 mmol) in DMF (0.5 ml) was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (329 mg, 1.02 mmol) and potassium carbonate (264 mg, 2 mmol) in DMF (2 ml). The mixture was heated at 100° C. for 3 hours and allowed to cool. The volatiles were removed by evaporation, and the residue partitioned between aqueous sodium hydrogen carbonate solution and methylene chloride. The organic phase was separated and passed through phase separating paper. The solvent was removed by evaporation, and the residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 4-(4-chloro-2-fluoroanilino)-7-(2-(1,3-dioxolan-2-yl)ethoxy)methoxyquinazoline (71 mg, 17%).

Workup

temperatureto cool
customThe volatiles were removed by evaporation
customthe residue partitioned between aqueous sodium hydrogen carbonate solution and methylene chloride
customThe organic phase was separated
customseparating paper
customThe solvent was removed by evaporation
customthe residue was purified by column chromatography
washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record: ord-3fab1147432840ec8dc87cc020a437fc
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042353E1

Reaction notes

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