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

HRID 2173474Notes

Reaction equation

HRID 2173474 reaction equation
[C:1]([C:5]1[N:6]=[C:7](N2CCOCC2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1NC2N(CC3C=CC=CC=3[Cl:48])N=NC=2C(=O)N=1)(C)(C)C.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)Cl>>[C:1]([C:5]1[N:6]=[C:7]([Cl:48])[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 14339535-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 1784418645-tert-butyl-3-[(2-chlorophenyl)methyl]-4H-triazolo[4,5-d]pyrimidin-7-one

Product 1

HCID 866832845-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

5-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine A mixture of 5-tert-butyl-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one (12.3 mg, 38.7 μmol) and N,N-diethylaniline (12.3 μL, 77.4 μmol) in POCl3 (250 μL, 2.73 mmol) was refluxed for 3 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-(2-chlorobenzyl)-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 3 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-5d224ccd46ea4ce0865e446cece60796
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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