3-Ethynylpyridine → 2-(6-Amino-8-(2-pyridin-3-yl-ethynyl)-purin-9-yl)ethanol

HRID 1920654Notes

Reaction equation

HRID 1920654 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:11][CH2:12][OH:13].[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)#[CH:16]>CCN(CC)CC.CN(C=O)C.[Cu]I>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:16]#[C:15][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[N:6]2[CH2:11][CH2:12][OH:13]

Participants

6

Reactant 2

HCID 1860033-EthynylpyridineHCID 445724692-(6-amino-8-bromo-9H-purin-9-yl)ethanol

Product 1

HCID 668679042-(6-Amino-8-(2-pyridin-3-yl-ethynyl)-purin-9-yl)ethanolYield 53.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 258 mg of 2-(6-amino-8-bromo-purin-9-yl)ethanol in a mixture of Et3N and DMF were added under an atmosphere of argon 35 mg of Pd(PPh)3Cl2, 19 mg CuI and 150 mg 3-ethynylpyridine. The mixture was stirred under argon at 60° C. for 3 hours and over night at room temperature. The precipitate was isolated, washed with water and hot ethanol and dried to give 150 mg (53%) of the desired product.

Workup

  1. customThe precipitate was isolated
  2. washwashed with water and hot ethanol
  3. customdried

Sources & evidence

ORD record
ord-95822e1621e24a1cbbdd20d092f23c8b
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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