Water → 5-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamine

HRID 1070602

Reaction equation

HRID 1070602 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[CH:3].I[C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.O.C(Cl)Cl>C(NCC)C.[Cu]I.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>[O:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[O:4][CH2:1][C:2]#[C:3][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 885792-Pyridinamine, 5-iodo-HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran

Product 1

HCID 223972415-(3-(Tetrahydro-2H-pyran-2-yloxy)-1-propynyl)-2-pyridinylamineYield 50%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

2-(2-Propynyloxy)tetrahydro-2H-pyran (360 mg), 5-iodo-2-pyridinylamine (440 mg), CuI (140 mg) and dichlorobis(triphenylphosphine)palladium (60 mg) are dissolved in diethylamine (10 mL). After the mixture is stirred for 1 h at room temperature, water (40 mL) and CH2Cl2 (80 mL) are added. The organic laywer is separated, dried (MgSO4) and concentrated. The resulting residue is purified on a silica gel plate (CH2Cl2/methanol, 9/1) to give 230 mg (50%) of the title compound as an oil which slowly solidifies. MS (ESI+) m/z 233 (M+H)+. 1H NMR (CDCl3) δ8.10, 7.60, 6.65, 5.90, 4.86, 4.48, 3.90, 3.5-3.6, 1.55-1.9.

Workup

  1. customThe organic laywer is separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue is purified on a silica gel plate (CH2Cl2/methanol, 9/1)

Sources & evidence

ORD record
ord-0bbf255b25584921bace1b5b94db5fa9
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Linked notes

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