4-(5-tert-butyl-3-(4-methoxy benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)morpholine → HCID 178441796, compound

HRID 2173533Notes

Reaction equation

HRID 2173533 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:8]2[N:13]=[N:12][N:11](CC3C=CC(OC)=CC=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:8]2[N:13]=[N:12][NH:11][C:9]=2[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 715580514-(5-tert-butyl-3-(4-methoxy benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)morpholine

Product 1

HCID 178441796HCID 178441796, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 4-(5-tert-butyl-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)morpholine (10.0 mg, 26.1 μmol) and TFA (250 μL) was refluxed for 5 h under N2 atmosphere. Then, the reaction mixture was concentrated in vacuo and purified by preparative HPLC (column: Gemini 5 um C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 85:15% to 5:95%. WL: 300 nm Flow: 30 mL/min.) to afford the title compound as white solid (0.9 mg, 13%). MS(m/c): 263.3 (MH+).

Workup

  1. temperaturewas refluxed for 5 h under N2 atmosphere
  2. concentrationThen, the reaction mixture was concentrated in vacuo
  3. custompurified by preparative HPLC (column: Gemini 5 um C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 85:15% to 5:95%. WL: 300 nm Flow: 30 mL/min.)

Sources & evidence

ORD record
ord-fa4e95b965d54220873310ba3f19b15d
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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