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Water → 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide

HRID 1773623
ノート
印刷プレビュー

反応式

HRID 1773623 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20](Cl)[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])=[N:7][C:8]=1[O:9][CH3:10].[C@@H:24]1([NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH2:30].O.ClCCl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20]([NH:30][C@@H:25]4[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:24]4[NH2:31])[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])=[N:7][C:8]=1[O:9][CH3:10]
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 962WaterHCID 6344DichloromethaneHCID 3429171,2-Diaminocyclohexane, cis-HCID 866613782-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide

生成物 1

HCID 566467642-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide収率 48.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 0.0817 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide in 2.33 mL of dioxane was added 0.168 mL (1.4 mmole) of cis-cyclohexane-1,2-diamine. The mixture was heated at 100 degrees for over night. Water and dichloromethane were added, separated. The aqueous layer was washed with dichloromethane twice. The organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10) gave 0.048 g of 2-(cis-2-amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide as a light yellow solid. MH+/Z=429.

後処理

  1. temperatureThe mixture was heated at 100 degrees for over night
  2. customseparated
  3. washThe aqueous layer was washed with dichloromethane twice
  4. washThe organic layer was washed with aqueous sodium carbonate, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10)

出典と根拠

ORDレコード
ord-d29b86af65614d84b33cb47e97241a7b
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09255110B2

反応ノート

読み込み中…

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