Potassium Carbonate → HCID 70974593, compound

HRID 1477226Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:12][CH2:13][O:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:5]2=[O:21].[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:16]1[CH:17]=[CH:18][CH:19]=[N:20][C:15]=1[O:14][CH2:13][CH2:12][N:6]1[C:5](=[O:21])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:28]3[CH:27]=[CH:26][C:25]([O:24][C:23]([F:22])([F:34])[F:35])=[CH:30][CH:29]=3)[CH:3]=2)[N:8]=[CH:7]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 60 mg 6-bromo-3-(2-(pyrimidin-2-yloxy)ethyl)quinazolin-4(3H)-one Compound 178-C (0.25 mmol), 53 mg 4-(trifluoromethoxy)phenyl boronic acid (0.38 mmol), 18 mg potassium carbonate (0.15 mmol), and 3 mg Pd(dppf)Cl2 in 5 mL of degassed 9:1 DMF:water solution was heated at 90° C. After 1 h, the reaction mixture was filtered through celite and the filtrate concentrated and purified by reverse-phase (ACN/H2O with 0.1% TFA) followed by neutralization on resin column to produce 56 mg of 3-(2-(pyrimidin-2-yloxy)ethyl)-6-(4-(trifluoromethoxy)phenyl)quinazolin-4(3H)-one Compound IV-25.

Workup

customof degassed 9:1 DMF
filtrationthe reaction mixture was filtered through celite
concentrationthe filtrate concentrated
custompurified by reverse-phase (ACN/H2O with 0.1% TFA)

Sources & evidence

ORD record: ord-4322a9f8dbd44fb8b5a34996587382e2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403782B2

Reaction notes

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