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Potassium Carbonate → 3-[3-(2,6-Dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile

HRID 426221
Notes
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Reaction equation

HRID 426221 reaction equation
[CH:1]([C:4]1[C:5](=[O:22])[NH:6][C:7](=[O:21])[NH:8][C:9]=1[C:10](=[O:20])[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=1)([CH3:3])[CH3:2].[Cl:23][C:24]1[N:29]=[C:28]([Cl:30])[CH:27]=[C:26]([CH2:31]Cl)[N:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Li+]>CN(C=O)C>[Cl:23][C:24]1[N:25]=[C:26]([CH2:31][N:8]2[C:9]([C:10]([C:11]3[CH:12]=[C:13]([CH:14]=[C:15]([CH3:17])[CH:16]=3)[C:18]#[N:19])=[O:20])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:22])[NH:6][C:7]2=[O:21])[CH:27]=[C:28]([Cl:30])[N:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 150017782,4-Dichloro-6-(chloromethyl)pyrimidineHCID 468803773-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 596868473-[3-(2,6-Dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile
Yield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-isopropyl-6-(3′-cyano-5′-methylbenzoyl)-2,4-pyrimidinedione (1.19 g, 4 mmol), 2,4-dichloro-6-chloromethyl-pyrimidine (790 mg, 4 mmol), anhydrous powdered potassium carbonate (552 mg, 4 mmol), and lithium iodide (536 mg, 4 mmol), was added DMF (20 ml). The mixture was stirred at room temperature for overnight and evaporated in vacuo. The residue was then purified by silica gel column chromatography (eluent, EA:hexane (1:2)) to afford 476 mg (26%) of 3-[3-(2,6-dichloro-pyrimidin-4-ylmethyl)-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile as a pale yellow foam.

Workup

  1. customevaporated in vacuo
  2. customThe residue was then purified by silica gel column chromatography (eluent, EA:hexane (1:2))

Sources & evidence

ORD record
ord-15b04728f63a413bb02beeaee7e30385
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