Sodium hydride → HCID 461299, compound

HRID 263393Notes

Reaction equation

HRID 263393 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[NH:6][CH:7]=[N:8]2.Br[CH2:14][CH2:15][CH2:16][CH2:17][B:18]([OH:20])[OH:19]>CN(C)C=O>[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH2:14][CH2:15][CH2:16][CH2:17][B:18]([OH:20])[OH:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53592776-ChloropurineHCID 14316432(4-Bromobutyl)boronic acid

Product 1

HCID 461299HCID 461299, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.22 g, 7.2 mmol) was added to a solution of 6-chloropurine (0.93 g, 6.0 mmol) in dimethylformamide (20 mL) and stirred for 10 minutes. 4-Bromobutyl boronic acid (1.1 g, 6.0 mmol) in dimethylformamide (5 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. After the removal of the dimethylformamide under high vacuum, the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1) to yield 0.78 g of pure product. Yield 51%; mp 135°-138° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.78-1.91 (m, B CH2 CH2 CH2), 4.26-4.32 (t, CH2 CH2 N), 7.40-7.42 (s, (HO)2 B), 8.68-8.70 (s, H C8 purine), 8.80-8.81 (s, H C2 purine). Elemental Analysis. (C9H12BO2N4Cl); Calcd. C, 42.47%; H, 4.75%; N, 22.02%; Found C, 42.48%; H, 4.80%; N, 22.06%.

Workup

  1. stirringstirred at room temperature for 16 hours
  2. customAfter the removal of the dimethylformamide under high vacuum
  3. customthe residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1)

Sources & evidence

ORD record
ord-a5eee8e304634e63a7a308323039aecc
Source dataset
uspto-grants-1997_07
Patent number
US05643893

Reaction notes

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