Potassium Carbonate → HCID 59511789, compound

HRID 1157467Notes

Reaction equation

[CH:1]1([CH2:4][NH:5][C:6]([CH2:8][N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:16]=3)[N:11]=[C:10]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:7])[CH2:3][CH2:2]1.O[C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.[C:44]([O-])([O-])=[O:45].[K+].[K+]>CC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([CH2:4][NH:5][C:6](=[O:7])[CH2:8][N:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:37]4[CH:38]=[CH:39][CH:40]=[C:35]([CH2:44][OH:45])[CH:36]=4)[CH:16]=3)[N:11]=[C:10]2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To trifluoromethanesulfonic acid 3-[(cyclopropylmethylcarbamoyl)methyl]-4-oxo-2-phenyl-3,4-dihydroquinazolin-6-yl ester (100 mg, 0.2 mmol) in acetone (2 mL) and water (1 mL) was added 3-hydroxyphenyl boronic acid (60 mg, 0.4 mmol), K2CO3 (excess), and tetrakis(triphenylphosphine)palladium (23 mg, 10 mol %). The solution was heated at 60° C. for 1 h. The resulting mixture was cooled to room temperature and the solid material collected by filtration, washed with acetone and dried in vacuo to give N-cyclopropylmethyl-2-[6-(3-hydroxymethylphenyl)-4-oxo-2-phenyl-4H-quinazolin-3-yl]acetamide (60 mg, 0.14 mmol, 68%).

Workup

temperatureThe resulting mixture was cooled to room temperature
filtrationthe solid material collected by filtration
washwashed with acetone
customdried in vacuo

Sources & evidence

ORD record: ord-e42d55b2c1fb49f6b142443ec6629803
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807686B2

Reaction notes

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