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

HRID 60154ノート

反応式

HRID 60154 の反応式
[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]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 118874966HCID 118874966、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3bab7b1576084080aa3e26dc6e6dec14
出典データセット
uspto-grants-2016_09
特許番号
US09440973B2

反応ノート

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