Triethylamine → HCID 23079460, compound

HRID 2354831Notes

Reaction equation

HRID 2354831 reaction equation
[OH:1][CH:2]([CH2:25][OH:26])[CH2:3][NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[C:10]([O:22][CH3:23])[N:11]2[CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[C:7]([NH2:24])[N:6]=1.C(N(CC)CC)C.[C:34](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:35]>CN(C)C=O>[CH3:23][O:22][C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[C:12]2[C:8]([N:9]=1)=[C:7]([NH2:24])[N:6]=[C:5]([NH:4][CH2:3][CH:2]1[CH2:25][O:26][C:34](=[O:35])[O:1]1)[N:13]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 23079485HCID 23079485, compound

Product 1

HCID 23079460HCID 23079460, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2,3-Dihydroxypropylamino)-8-methoxy-9-{(6-methyl-3-pyridyl)methyl}adenine (230 mg, 0.64 mmol) obtained by Reference example 18, 4-dimethylaminopyridine (5 mg, 0.04 mmol) and triethylamine (0.02 ml, 0.14 mmol) were dissolved in dimethylformamide (2 ml). Thereto was added di-t-butyl dicarbonate (410 mg, 1.9 mmol) in the oil bath kept at 50° C. and the mixture was stirred for 14 hours. The reaction mixture was concentrated and the residue was purified by preparative thin layer chromatography to give the captioned compound (64 mg, 0.17 mmol, yield 26%) as a white solid.

Workup

  1. customkept at 50° C.
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-d0ee8ee915d54495a69c7e954769045f
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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