Potassium Carbonate → HCID 22473448, compound

HRID 2183560Notes

Reaction equation

HRID 2183560 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]#[N:17])[CH:5]=[CH:6][CH:7]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:16]([C:9]1[CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH:3]=2)[NH:13][C:12](=[O:14])[NH:11][C:10]=1[CH3:15])#[N:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22473437HCID 22473437, compound

Product 1

HCID 22473448HCID 22473448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (1.62 g, 5.5 mmol), pyridine-4-boronic acid (0.75 g, 6.1 mmol), potassium carbonate (2.28 g, 16.5 mmol) and DMF (10 mL) was flushed with nitrogen gas several times before [1,1′-bis(diphenylphsophino)ferrocene]dichloropalladium (50 mg) was introduced. The reaction mixture was heated at 95° C. under nitrogen for 64 h, cooled to room temperature and filtered through Celite. The filtrate was diluted with MeOH and stirred with AG 50W-X2 Resin for 10 min. The resin was collected by vacuum filtration, washed with MeOH and then eluted with 2 M NH3 in MeOH. This NH3-MeOH solution was concentrated in vacuo to give 5-cyano-3,6-dihydro-4-methyl-2-oxo-6-(3-(4-pyridyl)phenyl)-(2H)-pyrimidine as a brown solid (1.6 1 g; 32%): 1H NMR (DMSO-d6, 400 MHz) δ 9.58 (s, 1H), 8.66 (d, 2H, J=2.2 Hz), 7.88 (s, 1H), 7.77 (d, 1H, J=7.9 Hz), 7.69 (m, 3H), 7.57 (m, 1H), 7.41 (d, 1H, J=7.9 Hz), 5.22 (s, 1H), 2.03 (d, 3H, J=2.2 Hz).

Workup

  1. customwas flushed with nitrogen gas several times before [1,1′-bis(diphenylphsophino)ferrocene]dichloropalladium (50 mg)
  2. additionwas introduced
  3. temperaturecooled to room temperature
  4. filtrationfiltered through Celite
  5. additionThe filtrate was diluted with MeOH
  6. filtrationThe resin was collected by vacuum filtration
  7. washwashed with MeOH
  8. washeluted with 2 M NH3 in MeOH
  9. concentrationThis NH3-MeOH solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f7e917501e3a4e358ca9d11d47d5151c
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

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