Acetaldehyde → 1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol

HRID 1426103Notes

Reaction equation

HRID 1426103 reaction equation
Cl.[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.C([Li])CCC.[CH:31](=[O:33])[CH3:32]>>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([CH:31]([OH:33])[CH3:32])[CH:13]=[N:12][C:11]=1[NH:17][C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 160614653-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 592256651-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanolYield 58.9%

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 (0.727 mL, 1.16 mmol), butyllithium (0.465 mL, 1.16 mmol), and acetaldehyde (0.0410 g, 0.930 mmol) were reacted according to the method of Example 7 to provide 1-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol (0.187 g, 58.8%). Mass spectrum (apci) m/z=342.1 (M+H).

Sources & evidence

ORD record
ord-47162b9577714390954d1a7960a6dc14
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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