Potassium Carbonate → 3-(3-{3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-phenyl)-acrylonitrile

HRID 426219ノート

反応式

HRID 426219 の反応式
[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]#[N:24])[CH:17]=[C:18]([CH3:20])[CH:19]=1)=[O:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Li+].[C:33]1(=[O:51])[N:37]([C:38]2[CH:43]=[C:42]([CH2:44]Cl)[CH:41]=[CH:40][N:39]=2)[C:36](=[O:46])[C:35]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:34]12>CN(C=O)C>[O:51]=[C:33]1[C:34]2[C:35](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:36](=[O:46])[N:37]1[C:38]1[CH:43]=[C:42]([CH2:44][N:6]2[C:5]([C:12]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][C:23]#[N:24])[CH:17]=[C:18]([CH3:20])[CH:19]=3)=[O:13])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[NH:8][C:7]2=[O:11])[CH:41]=[CH:40][N:39]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 591846992-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dioneHCID 667053903-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

生成物 1

HCID 667055303-(3-{3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-phenyl)-acrylonitrile収率 27%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 3-[3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (323 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol), and 2-phthalimido-4-chloromethylpyridine, was added anhydrous DMF (5 ml) and the mixture was stirred for overnight at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1)) to afford 152 mg (27%) of a white solid. 1H-NMR (200 MHz, DMSO-d6) δ 1.01 (3H, d, J=6.8 Hz), 1.10 (3H, d, J=6.8 Hz), 2.12 (1H, m), 2.33 (3H, s), 4.76 (2H, s), 6.57 (1H, d, J=16.6 Hz), 7.25 (1H, d, J=5.2 Hz), 7.31 (1H, s), 7.61 (1H, d, J=16.6 Hz), 7.80 (1H, s), 7.88-8.02 (6H, m), 8.41 (1H, d, J=5.2 Hz), 11.72 (1H, s).

後処理

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1))

出典と根拠

ORDレコード
ord-a1e0c20d22b54cae8e5ccae424321998
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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