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Diisopropylethylamine → 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine

HRID 2182060
ノート
印刷プレビュー

反応式

HRID 2182060 の反応式
FC(F)(F)C(O)=O.[C:8]([C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1)(=[O:10])[NH2:9].Cl[C:18]1[C:19]2[C:27]([CH3:28])=[CH:26][N:25]([C:29]3[C:33]([CH:34]([CH3:36])C)=[CH:32][S:31][C:30]=3[CH3:37])[C:20]=2[N:21]=[C:22]([CH3:24])[N:23]=1.[CH:38](N(C(C)C)CC)([CH3:40])[CH3:39].C(=O)([O-])O.[Na+]>C(O)C>[C:8]([C:11]1[CH2:16][CH2:15][N:14]([C:18]2[C:19]3[C:27]([CH3:28])=[CH:26][N:25]([C:29]4[CH:33]=[CH:34][C:36]([CH:38]([CH3:40])[CH3:39])=[CH:37][C:30]=4[S:31][CH3:32])[C:20]=3[N:21]=[C:22]([CH3:24])[N:23]=2)[CH2:13][CH:12]=1)(=[O:10])[NH2:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 224827414-Carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetateHCID 865899054-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 159078794-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine
収率 37.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In 4 ml of ethanol, 0.25 g of 4-carbamoyl-1,2,3,6-tetrahydropyridine trifluoroacetate and 0.35 g of 4-chloro-2,5-dimethyl-7-(isopropyl-2-methylthiophenyl)-7H-pyrrolo[2,3-d]pyrimidine were dissolved, and 0.39 g of diisopropylethylamine were added thereto. The reaction mixture was heated under reflux for 7.5 hours, and subsequently, a saturated aqueous solution of sodium hydrogencarbonate was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subsequently dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol=60:1), followed by crystallization from a mixed solvent of ethyl acetate-diethyl ether to yield 0.17 g of 4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-2,5-dimethyl-7-(4-isopropyl-2-methylthiophenyl)-7H-pyrrolo [2,3-d]pyrimidine.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 7.5 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialsubsequently dried over anhydrous sodium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol=60:1)
  9. customfollowed by crystallization from a mixed solvent of ethyl acetate-diethyl ether

出典と根拠

ORDレコード
ord-17c9c4b2377a4893a1dd5d92891a2fc6
出典データセット
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06894168B2

反応ノート

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