HCID 178418546, compound → 2-Fluoro-5-(2-(4-oxo-5-(pyrimidin-5-ylmethyl)-1,4-dihydropyrimidin-2-yl)ethyl)benzonitrile

HRID 474557Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:5][CH2:6][C:7]1[NH:8][CH:9]=[C:10]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)[C:11](=[O:13])[N:12]=1.[Cu][C:26]#[N:27]>CN1C(=O)CCC1>[F:24][C:23]1[CH:22]=[CH:21][C:4]([CH2:5][CH2:6][C:7]2[NH:8][CH:9]=[C:10]([CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[N:19][CH:20]=3)[C:11](=[O:13])[N:12]=2)=[CH:3][C:2]=1[C:26]#[N:27]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-(3-bromo-4-fluorophenethyl)-5-(pyrimidin-5-ylmethyl)pyrimidin-4(1H)-one (1.5 g, 3.7 mmol), copper(I) cyanide (399 mg, 4.4 mmol) in NMP (5 mL) was heated with a microwave reactor at 200° C. for 1.5 h. After cooling to room temperature, the mixture was filtered. The filtrate was partitioned between ethyl acetate (20 mL) and water (30 mL). The organic phase was collected, washed with water (30 mL×2), brine (20 mL), dried over Na2SO4, filtered, and concentrated to give the title compound as a gray solid (1.0 g, 55% yield), which was used without further purification. LCMS: rt=1.31 min, [M+H+]=336

Workup

temperatureAfter cooling to room temperature
filtrationthe mixture was filtered
customThe filtrate was partitioned between ethyl acetate (20 mL) and water (30 mL)
customThe organic phase was collected
washwashed with water (30 mL×2), brine (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-83db57f970944a58a086adadfd22eaff
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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