Sodium Carbonate → 3-Benzoyl-1-(3-chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dione

HRID 12674

Reaction equation

HRID 12674 reaction equation
[C:1]([N:9]1[C:14](=[O:15])[C:13](I)=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][Cl:20])[C:10]1=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:9]1[C:14](=[O:15])[C:13]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)=[CH:12][N:11]([CH2:17][CH2:18][CH2:19][Cl:20])[C:10]1=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27343783-Pyridinylboronic acidHCID 593375923-Benzoyl-1-(3-chloro-propyl)-5-iodo-1H-pyrimidine-2,4-dione

Product 1

HCID 451178313-Benzoyl-1-(3-chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dioneYield 20.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

3-Benzoyl-1-(3-chloro-propyl)-5-iodo-1H-pyrimidine-2,4-dione (Prep 41,500 mg, 1.2 mmol) was dissolved in degassed DME-water solution (5-1, 35 mL). Pyridine-3-boronic acid (629 mg, 1.8 mmol), Na2CO3 (380 mg, 3.6 mmol), 2-(dicyclohexylphosphino)biphenyl (84 mg, 0.24 mmol) and Pd(PPh3)4 (250 mg, 0.24 mmol) were added and the mixture was refluxed for 3 hours. The solvents were evaporated under vacuum and the residue was filtered over a SCX cartridge washing with MeOH and eluting with MeOH/NH3 95:5. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (from 98-2-0.2 to 95:5:05) to give the title compound (90 mg, 20% yield).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe solvents were evaporated under vacuum
  3. filtrationthe residue was filtered over a SCX cartridge
  4. washwashing with MeOH
  5. washeluting with MeOH/NH3 95:5
  6. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (from 98-2-0.2 to 95:5:05)

Sources & evidence

ORD record
ord-be7ca5510b144cf3b4c77a2eaa0cbb21
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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