1-Bromo-2-Chloroethane → HCID 69153971, compound

HRID 1296400Notes

Reaction equation

HRID 1296400 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:10](=[O:22])[N:9]([CH3:23])[C:8]=2[N:7]=[C:6]1[SH:24])[CH3:2].Br[CH2:26][CH2:27][Cl:28]>C(#N)C>[CH2:1]([O:3][CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:10](=[O:22])[N:9]([CH3:23])[C:8]=2[N:7]=[C:6]1[S:24][CH2:26][CH2:27][Cl:28])[CH3:2]

Participants

4

Reactant 2

HCID 78491-Bromo-2-ChloroethaneHCID 178468221HCID 178468221, compound

Product 1

HCID 69153971HCID 69153971, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (R)-7-ethoxymethyl-1-(5-hydroxyhexyl)-8-mercapto-3-methylxanthine (0.19 g, 0.533 mmol) potassium carbonate (0.15 g, 10.7 mmol) and 1-bromo-2-chloroethane (114 mg, 0.80 mmol) in acetonitrile (10 ml) was stirred at 65° C. for 1.5 hours. After concentrating under reduced pressure, the residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to provide (R)-7-ethoxymethyl-8-(2-chloroethylsulfanyl)-1-(5-hydroxyhexyl)-3-methylxanthine (150 mg, 67% yield) as a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-4339cb6bf9e545a3bd9b1bbf00c7e657
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

Loading…