Tributylamine → HCID 178483419, compound

HRID 1786302Notes

Reaction equation

HRID 1786302 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])=[C:9]([F:25])[CH:8]=1.[NH2:27][C:28]1[N:32]=[CH:31][NH:30][N:29]=1.C(N(CCCC)CCCC)CCC>>[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([C:14]2[C:20]([OH:21])=[N:27][C:28]3[N:29]([N:30]=[CH:31][N:32]=3)[C:15]=2[OH:16])=[C:9]([F:25])[CH:8]=1

Participants

4

Reactant 3

HCID 7622TributylamineHCID 16103033HCID 16103033, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178483419HCID 178483419, compoundYield 81%

Conditions

Temperature
160 °C

Procedure

A mixture of diethyl 2-{4-[4-(dimethylamino)butyl]-2,6-difluorophenyl]malonate (1.0 g, 2.7 mmol), 3-amino-1,2,4-triazole (250 mg, 3.0 mmol), and tributylamine (0.71 mL, 3.0 mmol) is stirred under nitrogen atmosphere at 160° C. for 16 h and cooled to room temperature. The mixture is stirred with 20 ml of hexanes. The precipitates are collected by filtration, washed with hexanes to give 6-{4-[4-(dimethylamino)butyl]-2,6-difluorophenyl}[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diol as a white solid (795 mg). MS: m/z 362.1 (M−H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitates are collected by filtration
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-2a61d1b6715b43a299f9e27b945d04ce
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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