Triethylamine → 2-(Cyclopentylmethyl)-6-oxo-4-(3-pyridinylamino)-1,6-dihydro-5-pyrimidinecarbonitrile

HRID 1724649Notes

Reaction equation

[C:1]([C:3](=[C:8](SC)[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6]C)=O)#[N:2].Cl.[CH:19]1([CH2:24][C:25]([NH2:27])=[NH:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CN(C=O)C.O>[CH:19]1([CH2:24][C:25]2[NH:27][C:4](=[O:6])[C:3]([C:1]#[N:2])=[C:8]([NH:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

0.1 g (0.40 mmol) of methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoate and 0.065 g (0.40 mmol) of 2-cyclopentylethanamidine hydrochloride and 0.16 g (1.60 mmol) of triethylamine are dissolved in 0.5 ml of DMF and stirred at 100° C. overnight. After cooling, the mixture is diluted with 10 ml of water and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated in vacuo, and the residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1). 78 mg (64% of theory) of the product are obtained as a colorless solid.

Workup

temperatureAfter cooling
extractionextracted with dichloromethane
dry with materialThe organic phase is dried over sodium sulfate
concentrationconcentrated in vacuo
customthe residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1)
custom78 mg (64% of theory) of the product are obtained as a colorless solid

Sources & evidence

ORD record: ord-5978ce1c15b648e08bc4f627ed4abec8
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488733B2

Reaction notes

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