Sodium Carbonate → HCID 66597085, compound

HRID 2276300Notes

Reaction equation

HRID 2276300 reaction equation
Cl[C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:24].[CH:25](/B(O)O)=[CH:26]\[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][S:11][C:9]2[N:8]=[C:7]3[C:3]([N:4]=[CH:5][N:6]3[CH3:24])=[C:2](/[CH:25]=[CH:26]/[CH3:27])[N:10]=2)=[CH:14][C:15]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 86663940HCID 86663940, compound

Product 1

HCID 66597085HCID 66597085, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

6-chloro-2-(4-methoxy-3-nitrobenzylsulfanyl)-9-methyl-9H-purine (100 mg, 0.273 mmol) was dissolved in dimethoxyethane (4 ml), then trans-propenylboronic acid (70 mg, 0.815 mmol) and tetrakis(triphenylphosphine)palladium (0) (30 mg, 0.025 mmol) were added. Then 106 mg (1.0 mmol) of sodium carbonate dissolved in water (2 ml) was added, and the mixture was heated to reflux for 2 hours. After cooling it, the insolubles were filtered off with Celite, the filtrate was distilled away under reduced pressure, ethyl acetate (20 ml) and water (20 ml) were added to the residue and extraction was performed. After washing with water, drying was carried out with anhydrous magnesium sulfate, the insolubles were filtered off, the filtrate was distilled away under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate: methanol=50:1) to obtain 2-(4-methoxy-3-nitrobenzylsulfanyl)-9-methyl-6-(1-trans-propenyl)-9H-purine (87.5 mg, 86%).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 hours
  4. temperatureAfter cooling it
  5. filtrationthe insolubles were filtered off with Celite
  6. distillationthe filtrate was distilled away under reduced pressure, ethyl acetate (20 ml) and water (20 ml)
  7. additionwere added to the residue and extraction
  8. washAfter washing with water
  9. customdrying
  10. filtrationthe insolubles were filtered off
  11. distillationthe filtrate was distilled away under reduced pressure

Sources & evidence

ORD record
ord-4da80f5f1b954ef9b72ed0d5fa6dffcd
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

Loading…