Methanol → 4-Chloro-2-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl-phenylamine

HRID 1692145Notes

Reaction equation

[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[N+:9]([C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[CH:14]=O)([O-])=O.CO.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>[NH4+].[Cl-].CCO.[Fe]>[Cl:20][C:17]1[CH:18]=[CH:19][C:12]([NH2:9])=[C:13]([C:14]2[N:4]3[CH:5]=[CH:6][CH:7]=[N:8][C:3]3=[N:1][N:2]=2)[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A 5 mL scintillation vial was charged with 2-hydrazinopyrimidine (61 mg, 0.55 mmol), 2-nitro-5-chlorobenzaldehyde (112 mg, 0.60 mmol) and MeOH (500 μL) and heated to 60° C. for 30 minutes. The MeOH was then removed in vacuo and the resultant solid was washed with Et2O. The crude solid (30 mg) was then suspended in CH2Cl2 (1 mL) and iodobenzene diacetate (39 mg, 0.12 mmol) was added. The reaction was stirred at room temperature for 30 minutes after which the solvent was removed in vacuo. The resultant residue was then dissolved in a 10% solution of saturated NH4Cl(aq) in EtOH and iron (19 mg, 0.33 mmol) was then added and the reaction was stirred at 80° C. for 4 h. The solvent was then removed in vacuo and the product was purified by silica gel chromatography to afford 4-chloro-2-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl-phenylamine as a light yellow oil.

Workup

customThe MeOH was then removed in vacuo
washthe resultant solid was washed with Et2O
customwas removed in vacuo
additionwas then added
stirringthe reaction was stirred at 80° C. for 4 h
customThe solvent was then removed in vacuo
customthe product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-aa0ec52dee334af6962bffcd9e6f9411
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153818B2

Reaction notes

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