Acetic Acid → 4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80771ノート

反応式

HRID 80771 の反応式
C([N:8]1[CH2:39][CH2:38][C:11]2[N:12]=[C:13]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[C:20]([CH3:37])=[CH:21][N:22]4[S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[N:14]=[C:15]([O:16][CH3:17])[C:10]=2[CH2:9]1)C1C=CC=CC=1.O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C.C([O-])(O)=O.[Na+].[OH-].[OH-].[Pd+2].[C]>[CH3:17][O:16][C:15]1[C:10]2[CH2:9][NH:8][CH2:39][CH2:38][C:11]=2[N:12]=[C:13]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20]([CH3:37])=[CH:21][N:22]3[S:27]([C:30]2[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[N:14]=1

参加物

8

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 712405256-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

生成物 1

HCID 712404804-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

試薬・触媒・溶媒 4

HCID 178502593HCID 178502593、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 6-benzyl-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (1.1 g, 2.0 mmol) in THF (15 mL) was added water (3.75 mL) and acetic acid (0.34 mL, 5.9 mmol), then 20 mol % Pd(OH)2/carbon (50% wet) (0.86 g, 0.61 mmol) was added. The reaction mixture was placed under an atmosphere of hydrogen gas via balloon. After 1.5 hours the mixture was diluted with ethyl acetate and neutralized with saturated aqueous NaHCO3. The mixture was then filtered through a pad of Celite®. The eluent was then further diluted with ethyl acetate and brine and the layers were separated. The organic layer was dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (0-20% MeOH/DCM) to provide 4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.91 (d, J=1.0 Hz, 3 H) 2.32 (s, 3 H) 2.68 (t, J=5.6 Hz, 2 H) 3.00 (t, J=5.7 Hz, 2 H) 3.72 (s, 2H) 3.92 (s, 3 H) 7.30-7.48 (m, 4 H) 7.65 (d, J=1.0 Hz, 1 H) 7.85 (d, J=8.3 Hz, 2 H) 8.04 (dd, J=7.3, 2.0 Hz, 1 H). MS (ESI+) m/z 449.2 (M+H)+.

後処理

  1. filtrationThe mixture was then filtered through a pad of Celite®
  2. additionThe eluent was then further diluted with ethyl acetate and brine
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel flash chromatography (0-20% MeOH/DCM)

出典と根拠

ORDレコード
ord-26906e031b7941958b3fd020eec999b9
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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