Methyl iodide → 2-Methylsulfanyl-5-(2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-1H-pyrimidin-4-one
Reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[C:10](=[O:16])[NH:11][C:12](=[S:15])[NH:13][CH:14]=2)[CH:5]=[CH:4][NH:3]1.[OH-].[K+].[CH3:19]I>C(O)C>[CH3:19][S:15][C:12]1[NH:13][CH:14]=[C:9]([CH2:8][C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=2)[C:10](=[O:16])[N:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 5-(2-Oxo-1,2-dihydro-pyridin-4-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (640 mg, 2.72 mmol, 1 eq) and KOH, 85% (1.05 eq, 190 mg) in 15 ml of absolute ethanol was stirred with at 80° C. for 1 hour. In the suspension was then added MeI (1.1 eq, 187 μl) dropwise and the mixture was stirred for another 2 hours. The solvent was then evaporated. In the crude was added 10 ml of water and pH of the solution was adjusted to 5.5-6.5. The precipitate was collected, it was dried and obtained was 2-Methylsulfanyl-5-(2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-1H-pyrimidin-4-one (394 mg, yield=48.2%, purity=83%) in form of white powder. MS: [M+H]+=250.15 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.46 (s, 3H), 3.31 (s, 2H), 6.05-6.10 (m, 2H), 7.25 (d, J=6.6 Hz, 1H), 7.84 (s, 1H)
Workup
- customThe solvent was then evaporated
- additionIn the crude was added 10 ml of water and pH of the solution
- customThe precipitate was collected
- customit was dried
- customobtained
Sources & evidence
- ORD record
- ord-0c8985b2459244ca8538557990a651ce
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174968B2
Reaction notes
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