Water → [3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-(1H-pyrazol-4-yl)-amine

HRID 1481250Notes

Reaction equation

HRID 1481250 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.C(OC([N:26]1[CH:30]=[C:29]([NH2:31])[CH:28]=[N:27]1)=O)(C)(C)C.O>COCCO>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[C:6]3[N:7]=[C:2]([NH:31][C:29]4[CH:30]=[N:26][NH:27][CH:28]=4)[N:3]=[CH:4][C:5]=3[N:10]=[N:9]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 59587648tert-butyl 4-amino-1H-pyrazole-1-carboxylateHCID 897179715-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 71666908[3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-(1H-pyrazol-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 262 mg (1.00 mmol) 5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 183 mg (1.00 mmol) 4-amino-pyrazole-1-carboxylic acid tert-butyl ester in 2.5 ml 2-methoxy-ethanol is stirred for 3 hours at 100° C. The reaction mixture is cooled to room temperature and water is added. The resulting precipitate is filtered off, washed with water and dried. The crude product is recrystallized from isopropanol giving “A3” as brown crystals; HPLC/MS (A): 1.6 min, [M+H] 309;

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried
  4. customThe crude product is recrystallized from isopropanol giving “A3” as brown crystals
  5. custom1.6 min, [M+H] 309

Sources & evidence

ORD record
ord-7660a1f517f943c4b24129788ee80fdc
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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