(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)methanol → HCID 178429463, compound

HRID 577023Notes

Reaction equation

HRID 577023 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[CH2:10]O)[CH:7]=[CH:6][S:5]2.BrCC1N2C(SC=C2)=NC=1Cl.[CH3:23][C:24]1[N:29]=[C:28]([SH:30])[N:27]=[C:26]([OH:31])[CH:25]=1>>[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[CH2:10][S:30][C:28]1[N:27]=[C:26]([OH:31])[CH:25]=[C:24]([CH3:23])[N:29]=1)[CH:7]=[CH:6][S:5]2

Participants

4

Reactant 3

HCID 332992(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)methanolHCID 66820731HCID 66820731, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429463HCID 178429463, compoundYield 22%

Procedure

{6-chloroimidazo[2,1-b][1,3]thiazol-5-yl}methanol was converted to 5-(bromomethyl)-6-chloroimidazo[2,1-b][1,3]thiazole, which was then reacted with 6-methyl-2-sulfanylpyrimidin-4-ol to give the title compound as a white solid (0.27 g, 22% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.67 (s, 2H), 6.04 (bs, 1H), 7.42 (d, J=4.7 Hz, 1H), 8.02 (d, J=4.7 Hz, 1H); M+ 312.8.

Sources & evidence

ORD record
ord-648107c1b1b74ee2b9f9ed7b505e6846
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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