Diisobutylaluminumhydride → HCID 57419934, compound

HRID 911000Notes

Reaction equation

HRID 911000 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11](OC)=[O:12])[S:5][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][N:17]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86634739HCID 86634739, compound

Product 1

HCID 57419934HCID 57419934, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Charged a flask with methyl 2-(4-methylthiazol-2-ylamino)isonicotinate (0.5 g, 2.01 mmol) and added ether (10 mL). The reaction mixture was cooled to 0° C. and diisobutylaluminum hydride (8.01 mL, 8.01 mmol) was added. The reaction mixture was stirred at 0° C. for 8 hours and then stirred overnight at room temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated. The residue was purified using silica gel column chromatography with ethyl acetate as the eluent to afford (2-(4-methylthiazol-2-ylamino)pyridin-4-yl)methanol (0.347 g, 76.6% yield) as white solid. 1H NMR (CD3OD) δ 8.20 (d, 1H), 7.01 (m, 1H), 6.86 (m, 1H), 6.42 (m, 1H), 4.60 (s, 2H), 2.27 (d, 3H); Mass spectrum (apci) m/z=222 (55) (M+H).

Workup

  1. stirringstirred overnight at room temperature
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-446555bd200c4b8eb2df1b45d8733db8
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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