Ethylenediamine → HCID 21874780, compound

HRID 733003Notes

Reaction equation

HRID 733003 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[N:15]=[N:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]4C(=O)C5=CC=CC=C5C4=O)[N:18]=3)[C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1.C(N)CN>CCO>[NH2:24][CH2:23][C:19]1[N:18]=[C:17]([CH2:16][N:13]2[C:8]3[N:9]=[C:10]([NH2:12])[N:11]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[C:7]=3[N:15]=[N:14]2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 21874566HCID 21874566, compound

Product 1

HCID 21874780HCID 21874780, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 7-(2-furyl)-3-(6-phthalimidomethyl-2-pyridylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (210 mg, 0.465 mmol) in EtOH (50 mL) was treated with ethylenediamine (62 μl, 0.929 mmol), stirred for 3 h at 90° C. and the resulting clear solution, cooled to room temperature and concentrated in vacuo to give 3-(6-aminomethyl-2-pyridylmethyl)-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine. A solution of this material in pyridine (10 mL) at 0° C. was treated with acetyl chloride (109 ml, 1.53 mmol), stirred for 10 min, poured into water (70 mL), extracted with EtOAc (3×20 mL) and the combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; EtOAc] to give the title compound (110 mg, 65%) as a beige solid.

Workup

  1. temperaturethe resulting clear solution, cooled to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-899306cb00324c6080b33723229e3f8b
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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