Ethyl Acetate → (5-Amino-2-phenyl-furo[2,3-d]pyrimidin-6-yl)-(2,4-dichloro-phenyl)-methanone

HRID 33113Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.Cl[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])=[O:19].[OH-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:9][C:8]1[C:7]2[CH:6]=[N:5][C:4]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[N:3][C:2]=2[O:1][C:17]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27])=[O:19]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of 4-hydroxy-2-phenyl-pyrimidine-5-carbonitrile (12) (50 mg, 0.25 mmol, from step 1) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (85 mg, 0.38mmol, 1.5 equiv) in anhydrous N,N-dimethylformamide (1.0 mL) was added NaOH (30.4 mg, 0.76 mmol, 3.0 equiv). The dark brown reaction mixture was stirred at 110° C. for 12 h. The reaction was then poured into ethyl acetate (10 mL) and water (10 mL). Extracted with ethyl acetate (3×10 mL). The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. The crude product was purified by pre-HPLC to provide 9.1 mg (9.3%) of the desired compound as yellow solid. 1H-NMR (CD3CN) δ 9.36 (s, 1H), 8.50 (d, 2H), 7.66 (d, 1H), 7.55 (m, 5H); MS LC-MS (MH+=384/386).

Workup

extractionExtracted with ethyl acetate (3×10 mL)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record: ord-203c4d19bdf84228acb70e14b7db09e2
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429584B2

Reaction notes

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