Ammonium Chloride → HCID 21874547, compound

HRID 732993Notes

Reaction equation

HRID 732993 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[C:8]3[N:16]=[N:15][N:14]([CH2:17][C:18]4[CH:23]=[C:22]([N+:24]([O-])=[O:25])[CH:21]=[CH:20][N:19]=4)[C:9]=3[N:10]=[C:11]([NH2:13])[N:12]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>CCO.CO.O.[Zn]>[OH:25][NH:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([CH2:17][N:14]2[C:9]3[N:10]=[C:11]([NH2:13])[N:12]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[CH:3][CH:4]=4)[C:8]=3[N:16]=[N:15]2)[CH:23]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 21874580HCID 21874580, compound

Product 1

HCID 21874547HCID 21874547, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7-(5-methyl-2-furyl)-3-(4-nitro-2-pyridylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (60 mg, 0.17 mmol) in EtOH (40 mL), MeOH (20 mL) and water (15 mL) was treated with ammonium chloride (280 mg, 5.23 mmol) and zinc (138 mg, 2.05 mmol), stirred for 1 h, filtered through Celite, concentrated in vacuo to ˜20 mL, diluted with brine (20 mL), extracted with EtOAc (3×20 mL) and the combined organic phase dried (MgSO4) and concentrated in vacuo to give the title compound (40 mg, 73%) as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo to ˜20 mL
  3. additiondiluted with brine (20 mL)
  4. extractionextracted with EtOAc (3×20 mL)
  5. dry with materialthe combined organic phase dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b28d5ffd78e4ae19806bc59749eb37f
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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