(+-)-2-Butanol → N-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7H-purin-6-amine

HRID 40214

Reaction equation

HRID 40214 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH2:17])=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[N:27]=[CH:26][N:25]=[C:24]2[C:20]=1[NH:21][CH:22]=[N:23]2.C(O)(CC)C>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][NH:17][C:19]4[N:27]=[CH:26][N:25]=[C:24]5[C:20]=4[NH:21][CH:22]=[N:23]5)=[N:14][N:15]=3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 53592776-ChloropurineHCID 67501979(6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

Product 1

HCID 57691174N-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7H-purin-6-amineYield 32.8%

Conditions

Temperature
100 °C

Procedure

A 15 mL tube was charged with (6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine (0.100 g, 0.444 mmol), 6-chloropurine (0.103 g, 0.666 mmol), and sec-butanol (3.00 ml, 32.4 mmol), sealed, then heated in a 100° C. oil bath for 5 hours. The reaction mixture was concentrated and the yellow residue was purified by MPLC using a 40 g RediSep column, eluting with a gradient of 3-8% MeOH/DCM over 80 minutes. N-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)-7H-purin-6-amine (0.0500 g, 32.8% yield) was isolated as the hydrochloride salt.

Workup

  1. customsealed
  2. concentrationThe reaction mixture was concentrated
  3. customthe yellow residue was purified by MPLC
  4. washeluting with a gradient of 3-8% MeOH/DCM over 80 minutes

Sources & evidence

ORD record
ord-9906acc1e70341139e36a3119039e418
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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