6-chloro-N4-o-tolylpyrimidine-4,5-diamine → HCID 57438664, compound

HRID 1098226Notes

Reaction equation

HRID 1098226 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[CH3:19])[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[CH3:19])[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 234775416-chloro-N4-o-tolylpyrimidine-4,5-diamineHCID 23668193Sodium Nitrite

Product 1

HCID 57438664HCID 57438664, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium nitrite (0.323 g, 4.69 mmol) was added to 6-chloro-N4-o-tolylpyrimidine-4,5-diamine (Intermediate AP5)(1 g, 4.26 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 7-chloro-3-o-tolyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (0.980 g, 94%) that was used without further purification.

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-0ef68f50d3a0490db7537973997e3a39
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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