Sodium Hydroxide → 5-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1481249Notes

Reaction equation

HRID 1481249 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([NH2:17])=[CH:4][N:3]=1.[N:18]([O-])=O.[Na+].[OH-].[Na+]>Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:17]=[N:18][N:8]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 897194042-Chloro-N4-(4-methoxyphenyl)pyrimidine-4,5-diamine

Product 1

HCID 897179715-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.51 g (6.02 mmol) 2-chloro-N4-(4-methoxy-phenyl)-pyrimidine-4,5-diamine in 75 ml 37% aqueous hydrochloric acid is treated with 852 mg (12.4 mmol) sodium nitrite. The mixture is stirred for 16 hours at room temperature. Aqueous sodium hydroxide is added to the reaction mixture to reach a neutral pH-value. Then the mixture is extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated giving 5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine as brown solid; HPLC/MS (A): 1.89 min, [M+H] 262;

Workup

  1. extractionThen the mixture is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-6f87b058189e4b6ea2712e96c68e8563
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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