Aniline → HCID 59834956, compound

HRID 271264Notes

Reaction equation

HRID 271264 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]([OH:14])=O)=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1.CCN=C=NCCCN(C)C.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:14])=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59834998HCID 59834998, compound

Product 1

HCID 59834956HCID 59834956, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-6-(2-furyl)-9H-purine-9-acetic acid (129 mg, 0.5 mmol) in DCM (2 mL) was treated with EDCI (96 mg, 0.5 mmol) and aniline (45 μL, 0.5 mmol), stirred at room temperature for 3 days, diluted with DCM, washed with water, dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2; 1% MeOH in EtOAc) to give the title compound (51 mg, 31%) as a white solid.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography (SiO2; 1% MeOH in EtOAc)

Sources & evidence

ORD record
ord-ca53696566f44a9c9ce7576055861060
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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