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

HRID 474559
Notes
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Reaction equation

HRID 474559 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[NH:12][CH:13]=[C:14]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=3)[C:15](=[O:17])[N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Cu][C:28]#[N:29]>CN1C(=O)CCC1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][C:11]2[NH:12][CH:13]=[C:14]([CH2:18][C:19]3[CH:20]=[N:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=3)[C:15](=[O:17])[N:16]=2)=[CH:3][C:2]=1[C:28]#[N:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178494122HCID 178494122, compound

Product 1

HCID 1784941232-Fluoro-5-(2-(5-((2-methoxypyrimidin-5-yl)methyl)-4-oxo-1,4-dihydropyrimidin-2-yl)ethyl)benzonitrileYield 30.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

The mixture of 2-[2-(3-bromo-4-fluorophenyl)ethyl]-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinone (300 mg, 0.716 mmol) and copper(I) cyanide (77 mg, 0.859 mmol) in NMP (2 mL) was heated with a microwave reactor at 200° C. for 2 h. Purification via Biotage then afforded the title compound (80 mg, 30.6% yield). LCMS: rt=2.21 min, [M+H+]=366

Workup

  1. customPurification via Biotage

Sources & evidence

ORD record
ord-d90cc69b05e94c7fb5257cf372115bcf
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes