Diisobutylaluminumhydride → HCID 68439304、化合物

HRID 2202420ノート

反応式

HRID 2202420 の反応式
C([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[N:10][CH:11]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH3:23][C:7]1[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[N:8]=1

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 68439408HCID 68439408、化合物

生成物 1

HCID 68439304HCID 68439304、化合物収率 78.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a 0° C. solution of 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carboxylic acid ethyl ester (0.20 g, 0.63 mmol) in THF (6 mL) was added diisobutylaluminum hydride (1 M in hexanes; 1.25 mL, 1.25 mmol) dropwise. The mixture was warmed to rt over 1 h. The reaction was quenched with 1 M H2SO4 (2 mL). The mixture was neutralized with satd. aq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL), and satd. aq. sodium potassium tartrate (10 mL). The mixture was stirred vigourously until the layers separated. The organic layer was dried (Na2SO4) and concentrated to give the crude product (138 mg), which was used in the next step without further purification. 1H NMR (CDCl3): 8.07 (s, 1H), 4.52 (s, 2H), 3.42-3.33 (m, 2H), 2.88-2.74 (m, 2H), 2.41 (s, 3H), 2.23 (s, 3H), 1.93-1.83 (m, 2H), 1.72-1.53 (m, 4H), 1.35-1.16 (m, 5H).

後処理

  1. customThe reaction was quenched with 1 M H2SO4 (2 mL)
  2. additionaq. NaHCO3, and diluted with MeOH (2 mL), CHCl3 (10 mL)
  3. customseparated
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-01b146b77fcd46d9b54b43c422ff334a
出典データセット
uspto-grants-2016_06
特許番号
US09365548B2

反応ノート

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