Potassium Iodide → 5-[2-[4-(1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]ethyl]-2-methylthio-3,6-dimethyl-3H-pyrimidin-4-one

HRID 2222281Notes

Reaction equation

[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:16][S:17][C:18]1[N:23]([CH3:24])[C:22](=[O:25])[C:21]([CH2:26][CH2:27]Cl)=[C:20]([CH3:29])[N:19]=1.[I-].[K+].C(N(CC)CC)C>C(#N)C>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:4]2[CH2:3][CH2:2][N:1]([CH2:27][CH2:26][C:21]3[C:22](=[O:25])[N:23]([CH3:24])[C:18]([S:17][CH3:16])=[N:19][C:20]=3[CH3:29])[CH2:6][CH:5]=2)=[CH:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(1,2,3,6-tetrahydropyridin-4-yl)indole (1.0 g, 5 mmol) in acetonitrile (30 ml) was added 2-methylthio-5-(2-chloroethyl)-3,6-dimethyl-3H-pyrimidin-4-one (1.42 g, 6.1 mmol), potassium iodide (0.84 g, 5 mmol) and triethylamine (1.4 ml, 10 mmol). The mixture was heated at 80° C. for 8 hours, cooled, concentrated and purified by flash chromatografy (dichloromethane/methanol/ammonia=95/4.5/0.5)

Workup

temperaturecooled
concentrationconcentrated
custompurified by flash chromatografy (dichloromethane/methanol/ammonia=95/4.5/0.5)

Sources & evidence

ORD record: ord-7be1f198750b4418a2b3c94018e7365e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371769B2

Reaction notes

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