Methanol → 6-(Pyridin-3-yl)pyrimidin-4-amine

HRID 250070Notes

Reaction equation

HRID 250070 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)[OH:16])[CH:10]=1.[C:18]([O-:21])([O-])=[O:19].[Na+].[Na+].CO>COCCOC.CCO.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[OH-:16].[NH4+:5].[C:18]([O:21][CH2:3][CH3:4])(=[O:19])[CH3:10].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 27343783-Pyridinylboronic acid

Product 2

HCID 21904419Ammonium hydroxide ethyl acetateHCID 574765746-(Pyridin-3-yl)pyrimidin-4-amineYield 79%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 6-chloropyrimidin-4-amine (0.324 g, 2.5 mmol), pyridin-3-ylboronic acid (0.384 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. The mixture was heated in the microwave synthesizer at 125° C. for 20 min and concentrated. The residue was purified by silica gel chromatography (10-60% ethyl acetate in hexanes, then 5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford 6-(pyridin-3-yl)pyrimidin-4-amine (0.17 g, 0.987 mmol, 40% yield) as an off-white solid. LCMS R.T.=0.31;

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography (10-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ba40fe69a51840aab0244736e8695f2d
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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