(2,6-Dichloropyridin-3-yl)methanol → 2-[(2,6-dichloro-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 630059Notes

Reaction equation

HRID 630059 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.BrCC1C(Cl)=NC(Cl)=CC=1.[CH3:21][C:22]1[N:27]=[C:26]([SH:28])[N:25]=[C:24]([OH:29])[CH:23]=1>C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([CH2:8][S:28][C:26]2[N:25]=[C:24]([OH:29])[CH:23]=[C:22]([CH3:21])[N:27]=2)=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

5

Reactant 3

HCID 12259932(2,6-Dichloropyridin-3-yl)methanolHCID 122653943-(Bromomethyl)-2,6-dichloropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 1784294332-[(2,6-dichloro-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The crude (2,6-dichloropyridin-3-yl)methanol was converted to 3-(bromomethyl)-2,6-dichloropyridine, which was then reacted with 6-methyl-2-sulfanylpyrimidin-4-ol in the presence of triethylamine to provide 2-{[(2,6-dichloropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (0.822 g, 82% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 4.36 (s, 2H), 5.95 (bs, 1H), 7.40 (d, J=8.0 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H); M+302.5.

Sources & evidence

ORD record
ord-5bcc98d027df40888ab5fdceafbbe220
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…