Water → HCID 49819589, compound

HRID 2276294Notes

Reaction equation

HRID 2276294 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][S:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([CH2:17][CH3:18])[N:13]2[CH3:16])=[C:9]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:8]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].O>O1CCCC1>[C:37]([NH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][S:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([CH2:17][CH3:18])[N:13]2[CH3:16])=[C:9]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:8]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 49819036HCID 49819036, compound

Product 1

HCID 49819589HCID 49819589, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-amino-4-methoxybenzylsulfanyl)-8-ethyl-9-methyl-6-morpholino-9H-purine (100 mg, 0.24 mmol) was dissolved in tetrahydrofuran (10 ml), triethylamine (49 mg, 0.48 mmol) and acetyl chloride (38 mg, 0.48 mmol) were added and stirred at room temperature overnight. After adding water to the reaction solution and extracting twice with ethyl acetate, 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=1:1) to obtain 77 mg (70% yield) of Compound 27.

Workup

  1. extractionextracting twice with ethyl acetate
  2. washthe organic layers were washed with a saturated saline solution
  3. dry with materialdried with MgSO4
  4. distillationAfter distilling away the solvent
  5. customunder reduced pressure, purification

Sources & evidence

ORD record
ord-0bbd6c4b77614c8e98dfab9dacccf267
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

Loading…