3-Ethoxy-2-propenenitrile → 2-Cyclobutylpyrimidin-4-amine

HRID 1786128Notes

Reaction equation

HRID 1786128 reaction equation
Cl.[CH:2]1([C:6]([NH2:8])=[NH:7])[CH2:5][CH2:4][CH2:3]1.C(O[CH:12]=[CH:13][C:14]#[N:15])C>>[CH:2]1([C:6]2[N:8]=[C:14]([NH2:15])[CH:13]=[CH:12][N:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 436013-Ethoxy-2-propenenitrileHCID 20542589Cyclobutanecarboximidamide hydrochloride

Product 1

HCID 457875782-Cyclobutylpyrimidin-4-amine

Procedure

This intermediate was made according to example 2, step A] method from cyclobutanecarboxamidine hydrochloride (0.3 g, obtained from cyclobutanecarbonitrile in analogy to Synth. Commun. 12 (13), 1982, 989-993 and Tetrahedron Lett. 31 (14), 1990, 1969-1972) and 3-ethoxy-acrylonitrile (0.3 g). 2-Cyclobutyl-pyrimidin-4-ylamine was obtained as a light brown solid (0.26 g): 1H NMR (δ, DMSO-d6): 7.98 (d, 1H), 6.66 (br s, 2H), 6.21 (s, 1H), 3.35-3-37 (m, 1H), 2.33-2.23 (m, 2H), 2.19-2.12 (m, 2H), 1.99-1.88 (m, 1H), 1.82-1.74 (m, 1H).

Sources & evidence

ORD record
ord-afc9e035799643efb9f2e283dffecc2a
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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