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Potassium Carbonate → 3-[3-[3-Fluoro-5-(4-methoxy-benzylamino)-benzyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile

HRID 426233
Notes
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Reaction equation

HRID 426233 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:6]=[C:7]([F:9])[CH:8]=1.[CH:20]([C:23]1[C:24](=[O:41])[NH:25][C:26](=[O:40])[NH:27][C:28]=1[C:29](=[O:39])[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([C:37]#[N:38])[CH:31]=1)([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:9][C:7]1[CH:8]=[C:3]([CH:4]=[C:5]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:6]=1)[CH2:2][N:27]1[C:28]([C:29]([C:30]2[CH:31]=[C:32]([CH:33]=[C:34]([CH3:36])[CH:35]=2)[C:37]#[N:38])=[O:39])=[C:23]([CH:20]([CH3:22])[CH3:21])[C:24](=[O:41])[NH:25][C:26]1=[O:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 468803773-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrileHCID 59184728(3-Bromomethyl-5-fluoro-phenyl)-(4-methoxy-benzyl)-amine

Product 1

HCID 591847713-[3-[3-Fluoro-5-(4-methoxy-benzylamino)-benzyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrileYield 55.9%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (3-bromomethyl-5-fluoro-phenyl)-(4-methoxy-benzyl)-amine (570 mg, 1.758 mmol), 5-isopropyl-6-(3′-cyano-5′-methylbenzoyl)-2,4-pyrimidinedione (522 mg, 1.758 mmol), and anhydrous powdered potassium carbonate (243 mg, 1.758 mmol), was added DMF (10 ml). The mixture was then stirred for overnight at room temperature and evaporated in vacuo. The residue was dissolved in methanol-dichloromethane (1:9), filtered through celite pad, and evaporated in vacuo to give a light yellow syrup. The crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:4)) to afford 531 mg of 3-{3-[3-fluoro-5-(4-methoxy-benzylamino)-benzyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-benzonitrile (151) as a yellow solid.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol-dichloromethane (1:9)
  3. filtrationfiltered through celite pad
  4. customevaporated in vacuo
  5. customto give a light yellow syrup
  6. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:4))

Sources & evidence

ORD record
ord-0ea59ea858cf4a24be80a45dc8e01918
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes