Sodium Carbonate → HCID 57476588, compound

HRID 1875960Notes

Reaction equation

HRID 1875960 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[Cl:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C([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>[Cl:9][C:10]1[CH:15]=[C:14]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 57476588HCID 57476588, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 6-chloropyrimidin-4-amine (0.324 g, 2.5 mmol), 3-chlorophenylboronic acid (0.489 g, 3.13 mmol), Na2CO3 (0.795 g, 7.50 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.050 mmol) was 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 (30-70% ethyl acetate in hexanes) to afford: 6-(3-chlorophenyl)pyrimidin-4-amine (0.47 g, 2.286 mmol, 91% yield) as a yellow solid. LCMS R.T.=1.45; [M+2H]+=208.05.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography (30-70% ethyl acetate in hexanes)
  3. customto afford

Sources & evidence

ORD record
ord-ff47c8fd2641414bb8731e837336fc81
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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