HCID 59589386, compound → HCID 178429495, compound

HRID 577024Notes

Reaction equation

HRID 577024 reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:8]=1.[CH3:15][C:16]1[N:21]=[C:20]([SH:22])[N:19]=[C:18]([OH:23])[CH:17]=1>>[CH3:15][C:16]1[N:21]=[C:20]([S:22][CH2:2][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:8]=2)[N:19]=[C:18]([OH:23])[CH:17]=1

Participants

3

Reactant 2

HCID 59589386HCID 59589386, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429495HCID 178429495, compoundYield 15%

Procedure

The title compound was prepared by following the procedure described for Example 55. 5-(pyridin-3-yl)pyridine-3-carbaldehyde provided [5-(pyridin-3-yl)pyridin-3-yl]methanol, which was reacted with phosphorus tribromide to give 3-(bromomethyl)-5-(pyridin-3-yl)pyridine. The reaction of 3-(bromomethyl)-5-(pyridin-3-yl)pyridine with 6-methyl-2-sulfanylpyrimidin-4-ol gave 6-methyl-2-({[5-(pyridin-3-yl)pyridin-3-yl]methyl}sulfanyl)pyrimidin-4-ol as a white solid (0.18 g, 15% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.45 (s, 2H), 6.04 (bs, 1H), 7.54 (m, 1H), 8.24 (d, J=4.7 Hz, 1H), 8.30 (s, 1H), 8.63 (d, J=4.7 Hz, 1H), 8.64 (s, 1H), 8.83 (s, 1H), 8.93 (s, 1H); M+ 310.1.

Sources & evidence

ORD record
ord-c355e71d81144d1aa071e8e6877fbb95
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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