2-Phenoxyethanamine → 5,7-diethyl-N-(2-phenoxyethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

HRID 1752802Notes

Reaction equation

HRID 1752802 reaction equation
CS([C:5]1[N:17]=[C:8]2[N:9]=[C:10]([CH2:15][CH3:16])[CH:11]=[C:12]([CH2:13][CH3:14])[N:7]2[N:6]=1)(=O)=O.[O:18]([CH2:25][CH2:26][NH2:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:15]([C:10]1[CH:11]=[C:12]([CH2:13][CH3:14])[N:7]2[N:6]=[C:5]([NH:27][CH2:26][CH2:25][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]=[C:8]2[N:9]=1)[CH3:16]

Participants

3

Reactant 2

HCID 156512-PhenoxyethanamineHCID 867193202-Methanesulfonyl-5,7-diethyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 766847915,7-diethyl-N-(2-phenoxyethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

Conditions

Temperature
115 °C

Procedure

A mixture of 2-methanesulfonyl-5,7-diethyl-[1,2,4]-triazolo[1,5-a]pyrimidine (4.5 g, 17.7 mmol) and 2-phenoxyethylamine (24.3 g, 177.2 mmol) was added to a 100 mL RBF with a magnetic stirring bar, and the flask was fitted with a condenser. The mixture was allowed to stir at 110-120° C. for 72 hours. Progress of the reaction was monitored by analytical HPLC with UV detection where the title compound eluted with retention time of 5.1 min. The reaction was allowed to cool to room temperature and partitioned between dichloromethane (150 mL) and 2 N HCl (100 mL). The acidic layer was extracted with dichloromethane (100 mL), and the combined organic layers were washed with saturated aqueous NaCl (75 mL). The NaCl layer was extracted with dichloromethane (75 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was added to chloroform (25 mL) and methanol (0.5 mL), and a precipitate was removed by filtration. The material in the organic layer was purified by silica gel chromatography with a gradient elution of 0.75-3.0% ethanol in chloroform. Fractions were pooled and concentrated under reduced pressure, and the solid material was crystallized from hot ethanol (35 mL) to afford the title compound as an off white solid (3.26 g, 59% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 7.27 (m, 2H), 7.03 (t, 1H), 6.96 (m, 3H), 6.85 (s, 1H), 4.13 (t, 2H), 3.61 (q, 2H), 2.96 (q, 2H), 2.75 (q, 2H), 1.31 (t, 3H), 1.24 (t, 3H). EM (calc.): 311.2; MS (ESI) m/e: 312.3 (M+H)+.

Workup

  1. additionwas added to a 100 mL RBF with a magnetic stirring bar
  2. customthe flask was fitted with a condenser

Sources & evidence

ORD record
ord-2707f486cac64d53b006a21dd89338b9
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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