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

HRID 705802
Notes
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Reaction equation

HRID 705802 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178517732HCID 178517732, compound

Product 1

HCID 1785097222-Fluoro-5-(2-(4-oxo-5-(pyrimidin-5-ylmethyl)-1,4-dihydropyrimidin-2-yl)ethyl)benzonitrileYield 80.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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

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

Sources & evidence

ORD record
ord-0bd4ee9b3c48479880ae5689f6fae7e0
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes