Methyl 4-methyl-3-oxopentanoate → 1-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

HRID 80802ノート

反応式

HRID 80802 の反応式
[CH3:1][O:2][C:3]1[C:4]2[CH2:32][NH:31][CH2:30][CH2:29][C:5]=2[N:6]=[C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:28])=[CH:12][N:13]3[S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[N:8]=1.[CH3:33][CH:34]([CH3:42])[C:35](=[O:41])[CH2:36][C:37](OC)=[O:38]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:1][O:2][C:3]1[C:4]2[CH2:32][N:31]([C:37](=[O:38])[CH2:36][C:35](=[O:41])[CH:34]([CH3:42])[CH3:33])[CH2:30][CH2:29][C:5]=2[N:6]=[C:7]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:28])=[CH:12][N:13]3[S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[N:8]=1

参加物

7

反応物 2

HCID 2759969Methyl 4-methyl-3-oxopentanoateHCID 712404804-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

生成物 1

HCID 866902601-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

To a solution of 4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, prepared as described in Example 17, (300 mg, 0.67 mmol) in toluene (3 mL), in a 2-5 mL microwave vial, was added methyl 4-methyl-3-oxopentanoate (0.28 mL, 2 mmol) followed by DMAP (25 mg, 0.2 mmol). The reaction vessel was then sealed and heated via microwave irradiation at 150° C. for 35 min. The reaction mixture was then cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the organic layer was dried by passing through a phase separator and then concentrated. The resulting residue was purified via silica gel flash chromatography (45-90% ethyl acetate/heptanes) to furnish 1-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione. MS (ESI+) m/z 561.3 (M+H)+.

後処理

  1. customThe reaction vessel was then sealed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customThe layers were separated
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe resulting residue was purified via silica gel flash chromatography (45-90% ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-c446987a847e49b88828cdc6965fed80
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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