5-(Bromomethyl)-2-chloropyridine → HCID 178429434, compound

HRID 630060Notes

Reaction equation

HRID 630060 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1.[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1>>[Cl:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 64246615-(Bromomethyl)-2-chloropyridine2×HCID 178429541HCID 178429541, compound

Product 1

HCID 178429434HCID 178429434, compoundYield 62%

Procedure

The title compound was prepared by following the procedure described for Example 55 from 6-chloropyridine-3-carbaldehyde to provide (6-chloropyridin-3-yl)methanol, which was converted to 5-(bromomethyl)-2-chloropyridine. The reaction of 6-methyl-2-sulfanylpyrimidin-4-ol with 5-(bromomethyl)-2-chloropyridine provided 2-{[(6-chloropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (0.82 g, 62% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 4.33 (s, 2H), 5.99 (bs, 1H), 7.46 (d, J=8.3 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 8.45 (s, 1H), 9.30 (s, 1H); M+268.2.

Sources & evidence

ORD record
ord-976bfc3ad99f4056835110fff08d2264
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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