Potassium Carbonate → 2-(Cyclohexylmethyl)-4-[(4-methyl-3-pyridinyl)amino]-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile

HRID 1724647Notes

Reaction equation

[C:1]([C:3](=[C:8]([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[CH3:18])SC)[C:4]([O:6]C)=O)#[N:2].Cl.[CH:20]1([CH2:26][C:27]([NH2:29])=[NH:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:20]1([CH2:26][C:27]2[NH:29][C:4](=[O:6])[C:3]([C:1]#[N:2])=[C:8]([NH:11][C:12]3[CH:13]=[N:14][CH:15]=[CH:16][C:17]=3[CH3:18])[N:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

Conditions

Temperature: 90 °C

Procedure

0.4 g (1.51 mmol) of methyl 2-cyano-3-[(4-methyl-3-pyridinyl)amino]-3-(methylsulfanyl)-2-propenoate are dissolved with 0.29 g (1.67 mmol) of 2-cyclohexylethanamidine hydrochloride and 0.46 g (3.3 mmol) of potassium carbonate in 5 ml of DMF and heated at 90° C. for 7 days. After cooling and filtration, the product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A; water, eluent B: acetonitrile, gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B) purified. 433 mg (88% of theory) of the product are obtained.

Workup

temperatureAfter cooling
filtrationfiltration
customthe product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A; water, eluent B: acetonitrile, gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
custompurified
custom433 mg (88% of theory) of the product are obtained

Sources & evidence

ORD record: ord-54789654d7a249bfad7cad73d37df11d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488733B2

Reaction notes

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