Aluminium lithium hydride → (6-(4-Methylthiazol-2-ylamino)-4-phenoxypyridin-3-yl)methanol

HRID 910963ノート

反応式

HRID 910963 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:24]=[C:23]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]([C:18](OCC)=[O:19])=[CH:16][N:15]=2)[S:11][CH:12]=1>CCOCC.C1COCC1>[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[N:15]=[CH:16][C:17]([CH2:18][OH:19])=[C:23]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=2)[S:11][CH:12]=1

参加物

5

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 24826421Ethyl 6-(4-methylthiazol-2-ylamino)-4-phenoxynicotinate

生成物 1

HCID 24826422(6-(4-Methylthiazol-2-ylamino)-4-phenoxypyridin-3-yl)methanol収率 68.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1M lithium aluminum hydride (70 mL, 70 mmol) in ether at 0° C. was added a solution of ethyl 6-(4-methylthiazol-2-ylamino)-4-phenoxynicotinate (14 mmol) in THF (50 mL). The reaction mixture was stirred for 1.5 hours, then slowly quenched with sodium sulfate decahydrate and stirred for 1 hour. The reaction mixture was filtered, the solids were washed with THF and the organic layer was concentrated. Water and ethyl acetate were added to the residue, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried, concentrated to 50 mL of ethyl acetate, and filtered. The residue was purified using silica gel column chromatography with 30% ethyl acetate in hexanes as eluent to afford the desired product (3.0 g, 66% yield) as light yellow solid. 1H NMR (DMSO) δ 10.83 (s, 1H), 8.20 (s, 1H), 7.50 (m, 2H), 7.30 (m, 1H), 7.17 (m, 2H), 6.49 (d, 1H), 6.35 (s, 1H), 5.07 (t, 1H), 4.55 (d, 2H), 2.17 (d, 3H); Mass spectrum (esi) m/z=314 (100)(M+H).

後処理

  1. customslowly quenched with sodium sulfate decahydrate
  2. stirringstirred for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. washthe solids were washed with THF
  5. concentrationthe organic layer was concentrated
  6. additionWater and ethyl acetate were added to the residue
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. customdried
  10. concentrationconcentrated to 50 mL of ethyl acetate
  11. filtrationfiltered
  12. customThe residue was purified

出典と根拠

ORDレコード
ord-7033b82e7950462ba33b67db1a9f5f83
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

反応ノート

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