N,N-Diethylaniline → 5-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2178991Notes

Reaction equation

HRID 2178991 reaction equation
[C:1]([C:5]1[NH:10][C:9]2[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:12]=[N:13][C:8]=2[C:7](=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:37]>>[C:1]([C:5]1[N:6]=[C:7]([Cl:37])[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178490918HCID 178490918, compound

Product 1

HCID 866832995-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

A mixture of 5-tert-butyl-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one (50.0 mg, 160 μmol) and N,N-diethylaniline (50.8 μL, 319 μmol) in POCl3 (1000 μL, 10.9 mmol) was refluxed for 4 h under N2 atmosphere. The reaction mixture was concentrated in vacuo, diluted with EtOAc, washed with cold H2O and brine, dried over Na2SO4 and concentrated in vacuo to afford crude 5-tert-butyl-7-chloro-3-(4-methoxy benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine. The residue was used for the next reaction without further purification.

Workup

  1. temperaturewas refluxed for 4 h under N2 atmosphere
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with cold H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b2e397dab59415c995eda588caa3abb
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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