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Pyridine → 2-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyrimidin-4-yl]-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 869327
ノート
印刷プレビュー

反応式

HRID 869327 の反応式
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23]2[N:26]([CH3:37])[C:27]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([NH2:36])[N:31]=3)=[C:28]([I:29])[C:22]=2[C:21]1=[O:38])=[O:19])([CH3:16])([CH3:15])[CH3:14].N1C=CC=CC=1>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23]2[N:26]([CH3:37])[C:27]([C:30]3[CH:35]=[CH:34][N:33]=[C:32]([N:36]4[C:4](=[O:5])[C:3]5[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:1]4=[O:11])[N:31]=3)=[C:28]([I:29])[C:22]=2[C:21]1=[O:38])=[O:19])([CH3:16])([CH3:15])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 6955Phthaloyl chlorideHCID 672843262-(2-Amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

生成物 1

HCID 672851072-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyrimidin-4-yl]-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester収率 74.2%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Pthaloyl chloride (0.089 g, 0.437 mmol) was added to a cold (0° C.) solution of 2-(2-Amino-pyrimidin-4-yl)-3-iodo-1-methyl-4-oxo-1,4,6,7-tetrahydro-pyrrolo[3,2-c]-pyridine-5-carboxylic acid tert-butyl ester (prepared as described in Example 1) (0.158 g, 0.337 mmol) and pyridine (0.069 g, 0.875 mmol) in dry DCM (1.5 ml) and the reaction mixture was stirred at room temperature in argon atmosphere for 4 h. The organic layer was washed with a saturated solution of NaHCO3 (1×2.0 ml), brine (1×2.0 ml), and it was dried over Na2SO4. The filtrate was evaporated to dryness to give the crude product, which was purified by flash chromatography, over silica gel (DCM/MeOH (9.8:0.2) as eluent), to afford 2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrimidin-4-yl]-3-iodo-1-methyl-4-oxo-1,4,6,7-tetra-hydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.150 mg, 0.25 mmol, 74%).

後処理

  1. washThe organic layer was washed with a saturated solution of NaHCO3 (1×2.0 ml), brine (1×2.0 ml), and it
  2. dry with materialwas dried over Na2SO4
  3. customThe filtrate was evaporated to dryness
  4. customto give the crude product, which
  5. customwas purified by flash chromatography, over silica gel (DCM/MeOH (9.8:0.2) as eluent)

出典と根拠

ORDレコード
ord-9aaec7630235446bbf574d4bea04d313
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08969366B2

反応ノート

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