Sodium Hydroxide → 4-Isobutyl-2-(5-isobutyl-3-methylpyrazol-1-yl)-6-methylpyrimidine

HRID 2047627

Reaction equation

[C:1]([NH:4][NH2:5])([NH2:3])=[NH:2].Cl.[OH-].[Na+].[CH3:9][CH:10]([CH3:18])[CH2:11][C:12](=O)[CH2:13][C:14](=O)[CH3:15]>O>[CH2:11]([C:12]1[CH:13]=[C:14]([CH3:15])[N:3]=[C:1]([N:4]2[C:14]([CH3:15])=[CH:13][C:12]([CH2:11][CH:10]([CH3:18])[CH3:9])=[N:5]2)[N:2]=1)[CH:10]([CH3:18])[CH3:9].[CH2:11]([C:12]1[CH:13]=[C:14]([CH3:15])[N:3]=[C:1]([N:4]2[C:12]([CH2:11][CH:10]([CH3:18])[CH3:9])=[CH:13][C:14]([CH3:15])=[N:5]2)[N:2]=1)[CH:10]([CH3:18])[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To aminoguanidine hydrochloride (1.59 g, 14.4 mmol), water (5 ml), sodium hydroxide (576 mg, 14.4 mmol), and 6-methyl-2,4-heptanedione (manufactured by Tokyo Chemical Industry, purity: 97.0% or higher) (4.50 g, 31.6 mmol) were added, and then stirred at 80° C. for 8 hours. To the reaction mixture, water (30 ml) was added, and the extraction was carried out with ethyl acetate (10 ml). The extract was washed with saturated brine, dried with anhydrous sodium sulfate, and then concentrated. The obtained residue (3.83 g) was subjected to silica gel column chromatography (80 g of silica gel, chloroform to chloroform:methanol=100:1) to obtain 4-isobutyl-2-(3-isobutyl-5-methylpyrazol-1-yl)-6-methylpyrimidine (181 mg, 4%) and 4-isobutyl-2-(5-isobutyl-3-methylpyrazol-1-yl)-6-methylpyrimidine (2.05 g, 50%).

Workup

extractionthe extraction
washThe extract was washed with saturated brine
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-2169f77453814d4d9f836f3b947affd6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592582B2

Linked notes

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