2-Chloroacrylonitrile → 2-Ethyl-4-pyrimidinamine

HRID 1786126Notes

Reaction equation

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

Participants

Reactant 2

HCID 701982-Chloroacrylonitrile

HCID 12301253Propionimidamide hydrochloride

Product 1

HCID 139252962-Ethyl-4-pyrimidinamine

Procedure

This intermediate was made according to example 2, step A] via the alternative preparation method from propionamidine hydrochloride (1.45 g, obtained from propionitrile in analogy to Synth. Commun. 12 (13), 1982, 989-993 and Tetrahedron Lett. 31 (14), 1990, 1969-1972) and 2-chloro-acrylonitrile (1.17 mL). 2-Ethyl-pyrimidin-4-ylamine was obtained as a light brown solid (0.89 g): 1H NMR (δ, DMSO-d6): 7.96 (d, 1H), 6.68 (br s, 2H), 6.21 (s, 1H), 2.55 (q, 2H, 1.18 (t, 3H).

Sources & evidence

ORD record: ord-0ac0e58ac8c8447d8e38dfe034a3c657
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507733B2

Reaction notes

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