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

HRID 474762Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

5-(2-Methoxy-pyridin-4-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (900 mg, 3.61 mmol, 1 eq) was refluxed in an acetic acid, glacial (12 ml)/HCl conc. (12 ml) mixture for 7 hours. (150° C. on display of heating device). Solvent from the mixture was evaporated as much as possible. In the mixture was added 20 ml of water. pH of the mixture was adjusted to 4-5. The resulting precipitate was collected and was dried. It was obtained 5-(2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (645 mg, yield=72.1%, purity=95%) in form of white powder. MS: [M+H]+=236.15 1H NMR (300 MHz; DMSO-d6) δ/ppm 3.36 (s, 2H), 6.06 (dd, J=6.81 Hz, J=1.60 Hz, 1H), 6.11(s, 1H), 7.24 (d, J=6.81 Hz, 1H), 7.43 (d, J=5.66 Hz, 1H), 11.36 (br.s, 1H), 12.30 (d, J=4.89 Hz, 1H), 12.52 (br.s, 1H)

Workup

customSolvent from the mixture was evaporated as much as possible
additionIn the mixture was added 20 ml of water
customThe resulting precipitate was collected
customwas dried

Sources & evidence

ORD record: ord-d2aa963c2c5a47bb8fab5d393d5d31d6
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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