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

HRID 400848Notes

Reaction equation

HRID 400848 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-methoxybenzyl)-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-9e5dd8766f1b4386b1ef07ec300ffa1f
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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