Triethylamine → HCID 66596962, compound

HRID 2276299Notes

Reaction equation

HRID 2276299 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].C(N(CC)CC)C.Cl.[CH2:33]([O:35][CH:36]1[O:41][CH2:40][CH2:39][NH:38][CH2:37]1)[CH3:34]>O1CCCC1>[CH2:33]([O:35][CH:36]1[CH2:37][N:38]([C:2]2[N:10]=[C:9]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=3)[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH3:24])[CH2:39][CH2:40][O:41]1)[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12751540HCID 12751540, compoundHCID 86663940HCID 86663940, compound

Product 1

HCID 66596962HCID 66596962, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-chloro-2-(4-methoxy-3-nitrobenzylsulfanyl)-9-methyl-9H-purine (850 mg, 2.32 mmol) was dissolved in tetrahydrofuran (100 ml), triethylamine (1.57 g, 15.51 mmol) and 2-ethoxymorpholine hydrochloride (520 mg, 3.10 mmol) were added and heated to reflux for 7 hours. After distilling away the solvent under reduced pressure, water was added to the residue and extracted twice with ethyl acetate, then the organic layers were washed with a saturated saline solution and dried with MgSO4. After distilling away the solvent under reduced pressure, purification was performed by silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain 738 mg (69% yield) of 6-(2-ethoxymorpholino)-2-(4-methoxy-3-nitrobenzylsulfanyl)-9-methyl-9H-purine.

Workup

  1. temperatureheated
  2. temperatureto reflux for 7 hours
  3. distillationAfter distilling away the solvent under reduced pressure, water
  4. additionwas added to the residue
  5. extractionextracted twice with ethyl acetate
  6. washthe organic layers were washed with a saturated saline solution
  7. dry with materialdried with MgSO4
  8. distillationAfter distilling away the solvent
  9. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-7b09fb9b46594c6bbbacf3b0b0730476
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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