Sodium Chloride → HCID 10024998, compound

HRID 2293923Notes

Reaction equation

HRID 2293923 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][NH:6][C:7]1[N:15]=[CH:14][N:13]=[C:12]2[C:8]=1[NH:9][CH:10]=[N:11]2.Br[CH2:20][CH2:21][CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][NH:6][C:7]1[N:15]=[CH:14][N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][N:11]2[CH2:20][CH2:21][CH2:22][C:23]#[N:24]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 10020812HCID 10020812, compound

Product 1

HCID 10024998HCID 10024998, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N6 -(3-iodobenzyl)adenine (2, 50 mg, 140 μmol), 4-bromobutyronitrile (300 mg, 2.0 mmol), and potassium carbonate (150 mg, 1.1 mmol) in DMF (2 mL) was stirred for 12 h at 80° C. Following the addition of 10 mL of half saturated sodium chloride, an oil separated. The oil was chromatographed on a preparative silica TLC plate (chloroform:methanol, 95:5, Rf 0.31) to give compound 22 (40 mg, 66%). MS (EI) m/z 418 (M+), 350, 291, 232, 187.

Workup

  1. customan oil separated
  2. customThe oil was chromatographed on a preparative silica TLC plate (chloroform:methanol, 95:5, Rf 0.31)

Sources & evidence

ORD record
ord-56dc9e1ca3524c90904a97481b53d9df
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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