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

HRID 2059820Notes

Reaction equation

HRID 2059820 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)O)[CH:10]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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: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

6

Reactant 3

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

Product 1

HCID 574765746-(Pyridin-3-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 69104347Dioxane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 6-chloropyrimidin-4-amine (0.324 g, 2.5 mmol), pyridin-3-ylboronic acid (0.385 g, 3.13 mmol), Na2CO3 (0.795 g, 7.5 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.05 mmol) were suspended in a mixture of dioxane/EtOH/water. The mixture was heated in the microwave synthesizer at 125° C. for 20 min (reaction was run twice) and concentrated. The residue was purified on by silica gel chromatography using a 10-60% ethyl acetate/hexanes gradient, followed by a 5-25% 9:1 methanol:ammonium hydroxide in ethyl acetate gradient. The desired fractions were concentrated to give an off-white solid. MS(LC/MS) R.T.=0.28; (M+H=173.13).

Workup

  1. customreaction
  2. concentrationconcentrated
  3. customThe residue was purified on by silica gel chromatography
  4. concentrationThe desired fractions were concentrated
  5. customto give an off-white solid
  6. customR.T.=0.28

Sources & evidence

ORD record
ord-42077d34138d46d1814003c6450bb22b
Source dataset
uspto-grants-2012_10
Patent number
US08278320B2

Reaction notes

Loading…