Butanal → N,N-dibutyl-5-methyl-1H-pyrazol-3-amine

HRID 528950Notes

Reaction equation

[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[CH:8](=O)[CH2:9][CH2:10][CH3:11]>>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH3:4])[C:4]1[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=1)[CH2:9][CH2:10][CH3:11]

Participants

Reactant 2

HCID 261Butanal

HCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 71062304N,N-dibutyl-5-methyl-1H-pyrazol-3-amineYield 106.1%

Procedure

Following a procedure analogous to that for the synthesis Example 106, 5-methyl-1H-pyrazol-3-amine (Aldrich, 486 mg, 5.00 mmol) and butyraldehyde (541 mg, 7.50 mmol) were converted to the title compound (555 mg, 53%). 1H NMR (CDCl3) δ 5.34 (s, 1H), 3.17 (t, J=7.3 Hz, 4H), 2.21 (s, 3H), 1.55 (td, J=15.1, 7.5 Hz, 4H), 1.34 (qd, J=15.0, 7.3 Hz, 4H), 0.94 (t, J=7.4 Hz, 6H); MS(ESI+) m/z 210.1 (M+H)+.

Sources & evidence

ORD record: ord-4393940700654ae6926e0f13ce011ad4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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