3-Pyridinemethanamine → 6-Amino-9-(2-hydroxyethyl)-8-[(3-pyridinylmethyl)amino]-9H-purine

HRID 2112398Notes

Reaction equation

HRID 2112398 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:11][CH2:12][OH:13].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH2:22])[CH:16]=1>O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([NH:22][CH2:21][C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)[N:6]2[CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 445724692-(6-amino-8-bromo-9H-purin-9-yl)ethanol

Product 1

HCID 688816656-Amino-9-(2-hydroxyethyl)-8-[(3-pyridinylmethyl)amino]-9H-purineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.387 g (1.5 mmol) 6-amino-8-bromo-9-(2-hydroxyethyl)-9H-purine and 0.456 3-picolylamine (4.2 mmol) was heated to 150° C. under an argon atmosphere. After completion of the reaction (˜5 hours) the reaction mixture was diluted with water leading to the precipitation of the product. The precipitate was isolated, washed with water and diethylether to give 0.372 g (87%) of the desired product.

Workup

  1. customAfter completion of the reaction (˜5 hours) the reaction mixture
  2. customThe precipitate was isolated
  3. washwashed with water and diethylether

Sources & evidence

ORD record
ord-af826754e44241178f34a8651ce7721b
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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