Pyridine, 5-(bromomethyl)-2-methoxy- → HCID 178491703, compound

HRID 630061Notes

Reaction equation

HRID 630061 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][CH3:10])=[N:7][CH:8]=1.[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1>>[CH3:10][O:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][S:18][C:16]2[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 182933Pyridine, 5-(bromomethyl)-2-methoxy-2×HCID 178429541HCID 178429541, compound

Product 1

HCID 178491703HCID 178491703, compoundYield 75%

Procedure

The title compound was prepared by following the procedure described for Example 55 using 6-methoxypyridine-3-carbaldehyde to provide (6-methoxypyridin-3-yl)methanol, which was converted to 5-(bromomethyl)-2-methoxypyridine. The reaction of 5-(bromomethyl)-2-methoxypyridine and 6-methyl-2-sulfanylpyrimidin-4-ol provided 2-{[(6-methoxypyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid (0.975 g, 75% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H), 3.79 (s, 3H), 4.29 (s, 2H), 5.99 (bs, 1H), 6.74 (d, J=8.3 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H), 8.19 (s, 1H); M+263.87.

Sources & evidence

ORD record
ord-3188f32227c2499782b9968d91ade0d2
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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