Diisobutylaluminumhydride → 3-(3-hydroxypropyl)-6-(2-isopropylphenyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

HRID 60154노트

반응식

HRID 60154 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:28]=[CH:27][C:13]2[N:14]([CH3:26])[C:15](=[O:25])[N:16]([CH2:19][CH2:20][C:21](OC)=[O:22])[C:17](=[O:18])[C:12]=2[CH:11]=1)([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[OH:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17](=[O:18])[C:12]2[CH:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:1]([CH3:3])[CH3:2])[N:28]=[CH:27][C:13]=2[N:14]([CH3:26])[C:15]1=[O:25]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 118874966HCID 118874966, 화합물

생성물 1

HCID 1188749933-(3-hydroxypropyl)-6-(2-isopropylphenyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione수율 15.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-55 °C

실험 절차

To a solution of methyl 3-(6-(2-isopropylphenyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propanoate (140 mg, 0.367 mmol) in THF (3.7 mL) at −55° C. was added diisobutylaluminium hydride (1.1 mL, 1.58 mmol, 1.5M in toluene) dropwise. The reaction was stirred at −55° C. for 1 h, warmed to 0° C., quenched with aq. NH4Cl (10 mL) and diluted with EA (20 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated to give 3-(3-hydroxypropyl)-6-(2-isopropylphenyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (20 mg, 15% yield) as a white solid. 1H NMR (DMSO-d6) δ: 8.99 (s, 1H), 7.85 (s, 1H), 7.49-7.43 (m, 2H), 7.29-7.28 (m, 2H), 4.51-4.49 (m, 1H), 4.03-4.00 (m, 2H), 3.633 (s, 3H), 3.49-3.45 (m, 2H), 3.17-3.14 (m, 1H), 1.77-1.73 (m, 1H), 1.15-1.14 (m, 6H). LCMS: MH+ 354 and TR=2.246 min.

후처리

  1. temperaturewarmed to 0° C.
  2. customquenched with aq. NH4Cl (10 mL)
  3. additiondiluted with EA (20 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3bab7b1576084080aa3e26dc6e6dec14
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440973B2

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