Hydrochloric Acid → 5-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

HRID 705993Notes

Reaction equation

C[O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:17])[NH:12][C:13](=[S:16])[NH:14][CH:15]=2)=[CH:5][CH:4]=1.Cl>C(O)(=O)C>[O:2]=[C:3]1[NH:8][CH:7]=[C:6]([CH2:9][C:10]2[C:11](=[O:17])[NH:12][C:13](=[S:16])[NH:14][CH:15]=2)[CH:5]=[CH:4]1

Participants

Conditions

Temperature: 150 °C

Procedure

5-(6-methoxy-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (395 mg, 1.58 mmol, 1 eq) was refluxed in an acetic acid, glacial (5 ml)/HCl conc. (5 ml) mixture for 16 hours. (150° C. on display of heating device). Solvent from the mixture was evaporated as much as possible. In the mixture was added 10 ml of water. pH of the mixture was adjusted to 4-5. The resulting precipitate was collected and was dried. It was obtained 5-(6-oxo-1,6-dihydro-pyridin-3-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (285 mg, yield=61.3%, purity=90%) in form of grey powder. MS: [M+H]+=236.20 1H NMR (300 MHz; DMSO-d6) δ/ppm 3.24 (s, 2H), 6.25 (d, J=9.36 Hz, 1H), 7.28-7-36 (m, 2H), 11.39 (br.s, 1H), 12.23 (br.s, 1H), 12.46 (br.s, 1H)

Workup

customSolvent from the mixture was evaporated as much as possible
additionIn the mixture was added 10 ml of water
customThe resulting precipitate was collected
customwas dried

Sources & evidence

ORD record: ord-d15e385e185643a0b26cebe16c8981ac
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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