6-chloro-N4-(2-chlorophenyl)pyrimidine-4,5-diamine → 7-Chloro-3-(2-chloro-phenyl)-3h-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1098223Notes

Reaction equation

HRID 1098223 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]=1[NH2:20]>C(O)(=O)C.C(Cl)Cl>[Cl:5][C:6]1[C:7]2[N:20]=[N:1][N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 234775426-chloro-N4-(2-chlorophenyl)pyrimidine-4,5-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 574386157-Chloro-3-(2-chloro-phenyl)-3h-[1,2,3]triazolo[4,5-d]pyrimidineYield 57.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium nitrite (0.298 g, 4.31 mmol) was added to 6-chloro-N4-(2-chlorophenyl)pyrimidine-4,5-diamine (Intermediate AP1) (1 g, 3.92 mmol) in acetic acid (50% Aq, 25 mL) and DCM (25 mL) at room temperature. The resulting solution was stirred at room temperature for 15 minutes. The reaction mixture was separated and the organic phase was washed with water (10 mL), dried (MgSO4) and evaporated to give crude product (0.600 g) that was used without further purification. 1H NMR (400 MHz, CDCl3) δ δ7.52-7.65 (m, 3H), 7.68-7.73 (m, 1H), 8.97 (s, 1H); m/z (ES+), (M+H)+=266.21; HPLC tR=2.33 min

Workup

  1. customThe reaction mixture was separated
  2. washthe organic phase was washed with water (10 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a27926cbae42498fa775e56b6007b9d4
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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