Thiourea → 5-[(1-methyl-1H-indol-3-yl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

HRID 705939Notes

Reaction equation

[OH:1]/[CH:2]=[C:3](/[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH3:18])[CH:10]=1)\[C:4](OC)=O.[NH2:19][C:20]([NH2:22])=[S:21]>CO>[CH3:18][N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:8][C:3]2[C:2](=[O:1])[NH:19][C:20](=[S:21])[NH:22][CH:4]=2)=[CH:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of methyl (2Z)-3-hydroxy-2-[(1-methyl-1H-indol-3-yl)methyl]-2-propenoate (0.790 g, 3.22 mmol) in methanol (10 mL) was added thiourea (0.25 g, 3.28 mmol). The mixture was heated at 50° C. for 6 h. After cooling to room temperature, purification via reverse phase flash chromatography then afforded the title compound (200 mg, 0.590 mmol, 18.31% yield). LCMS: rt=2.36 min, [M+H+]=272

Workup

temperatureAfter cooling to room temperature
custompurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-b82a527016ab4cc598b0c81c52638025
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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