Methyl iodide → 3-(benzyloxy)-5-methyl-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426093Notes

Reaction equation

HRID 1426093 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14](Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.[CH2:26]([Li])CCC.IC>>[ClH:1].[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14]([CH3:26])[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 727028693-(benzyloxy)-5-methyl-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 12.8%

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 0.350 g, 0.930 mmol), MeLi (0.639 mL, 1.02 mmol), butyllithium (0.409 mL, 1.02 mmol), and iodomethane (0.165 g, 1.16 mmol) were reacted according to the method of Example 7 to provide 3-(benzyloxy)-5-methyl-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.037 g, 12.8% yield). 1H NMR (DMSO-d6) δ 7.83 (s, 1H), 7.60 (m, 2H), 7.54 (s, 1H), 7.42 (m, 2H), 7.37 (m, 1H), 6.84 (s, 1H), 5.32 (s, 2H), 2.32 (s, 3H), 2.29 (s, 3H). Mass spectrum (apci) m/z=312.1 (M+H-HCl).

Sources & evidence

ORD record
ord-af5be5b0bffd44a9ac95e9caa2b0d0ce
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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