1,10-Phenanthroline → HCID 59588819, compound

HRID 886818Notes

Reaction equation

HRID 886818 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>ClCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C:14]2[CH:13]=[C:12]([CH3:21])[CH:17]=[CH:16][CH:15]=2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 13181,10-PhenanthrolineHCID 27339503-Tolylboronic acidHCID 53244122,6-Dichloropurine

Product 1

HCID 59588819HCID 59588819, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dichloropurine (1.3 mmol), m-Tolyl boronic acid (4.0 mmol), anhydrous cupric acetate (1.32 mmol), 4 Å molecular sieves (1 g) [1,10]-Phenanthroline (2.64 mmol) in 25 ml of anhydrous dichloromethane were stirred at room temperature in a round bottomed flask. The reaction mixture was stirred at room temperature and monitored by TLC, LC-MS. Reaction was complete after 24 h. The molecular sieves and inorganic material were removed by filtration through a celite bed. The bed was thoroughly washed with methanol. The combined organics were purified by flash chromatography to yield 50% of the desired compound as a solid. m/z: 279.02 [MH]+.

Workup

  1. customReaction
  2. customThe molecular sieves and inorganic material were removed by filtration through a celite bed
  3. washThe bed was thoroughly washed with methanol
  4. customThe combined organics were purified by flash chromatography

Sources & evidence

ORD record
ord-644b68d7e2cc4ab7826e0cb2179e0fbe
Source dataset
uspto-grants-2012_08
Patent number
US08247410B2

Reaction notes

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