Hydrazine → 4-(2,6-Diamino-pyrimidin-4-yloxy)-benzoic acid hydrazide

HRID 1994009Notes

Reaction equation

HRID 1994009 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([NH2:19])[N:3]=1.[NH2:20][NH2:21]>CO>[NH2:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:20][NH2:21])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[C:4]([NH2:19])[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59135324Methyl 4-[(2,6-diaminopyrimidin-4-yl)oxy]benzoate

Product 1

HCID 591353394-(2,6-Diamino-pyrimidin-4-yloxy)-benzoic acid hydrazideYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[(2,6-diaminopyrimidin-4-yl)oxy]benzoate (2.74 g, 10.52 mmol) was suspended in ca. 180 mL of anhydrous methanol and anhydrous hydrazine (1.021 g, 1.0 mL, 31.85 mmol, 3.03 eq) was added to this suspension. The reaction mixture was refluxed for 3 hours, then MeOH was very slowly distilled off till the total volume reached ca. 30 mL. This solution was allowed to stand at ambient temperature for 48 hrs. A white precipitate slowly crystallized out. It was collected, washed with 40 mL of EtOAc, 40 mL of anhydrous Et2O and dried in vacuo to give the title product as a fine white powder (2.02 g). Yield 73.7%.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. distillationMeOH was very slowly distilled off till the total volume
  3. customA white precipitate slowly crystallized out
  4. customIt was collected
  5. washwashed with 40 mL of EtOAc, 40 mL of anhydrous Et2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2a4a6973e99e4a87818c9d7bea3b12fd
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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