Diisobutylaluminumhydride → HCID 68439304, 화합물

HRID 1853443노트

반응식

HRID 1853443 반응식
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

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 68439408HCID 68439408, 화합물

생성물 1

HCID 68439304HCID 68439304, 화합물수율 78.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e2bf0c3c7a374b4cbfd4ce878dcd20c9
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962644B2

반응 노트

불러오는 중…