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Sodium Carbonate → HCID 57460915, compound

HRID 1718936
Notes
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Reaction equation

HRID 1718936 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[C:8](=[O:23])[N:9]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:10]([CH3:16])=[N:11][C:12]=2[CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)#[N:27].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:16][C:10]1[N:9]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:8](=[O:23])[C:7]([CH2:6][C:5]2[CH:24]=[CH:25][C:2]([C:29]3[C:28]([C:26]#[N:27])=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:3][CH:4]=2)=[C:12]([CH2:13][CH2:14][CH3:15])[N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27346102-Cyanophenylboronic acidHCID 574609165-(4-bromobenzyl)-2-methyl-6-propyl-3-(tetrahydro-2H-pyran-4-yl)pyrimidin-4(3H)-one

Product 1

HCID 57460915HCID 57460915, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(4-bromobenzyl)-2-methyl-6-propyl-3-(tetrahydro-2H-pyran-4-yl)pyrimidin-4(3H)-one (0.7 g), (2-cyanophenyl)boronic acid (0.36 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.07 g), 2 M aqueous sodium carbonate solution (1.5 mL) and 1,4-dioxane (15 mL) was stirred at 100° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.61 g, 83%).

Workup

  1. washwashed with water
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a31765d0e6724792bdc4f9d046f54b30
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803940B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes