Sodium Carbonate → 6-(Pyridin-3-yl)pyrimidin-4-amine

HRID 1875939Notes

Reaction equation

HRID 1875939 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.CO[C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13]N=1.[C:20]([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:16]1[CH:11]=[CH:20][CH:13]=[C:14]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 27367782-Methoxypyrimidine-5-boronic acid

Product 1

HCID 574765746-(Pyridin-3-yl)pyrimidin-4-amineYield 51%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

6-Chloropyrimidin-4-amine (0.35 g, 2.70 mmol), 2-methoxypyrimidin-5-ylboronic acid (0.520 g, 3.38 mmol), Na2CO3 (0.859 g, 8.11 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.038 g, 0.054 mmol) were suspended in a mixture of DME/EtOH/water. (15:2:3 mL). The mixture was heated in the microwave synthesizer at 125° C. for 20 min and concentrated. The residue was purified by silica gel chromatography (0-5% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford 6-(pyridin-3-yl)pyrimidin-4-amine (0.28 g, 1.378 mmol, 51% yield) as an off-white solid. LCMS R.T.=0.53; [M+H]+=204.11.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography (0-5% 9:1 methanol:ammonium hydroxide-ethyl acetate)

Sources & evidence

ORD record
ord-623916c487944e9baa4ff2139348f9de
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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