Sodium Hydroxide → tert-Butyl 2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1193353ノート

反応式

HRID 1193353 の反応式
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].CN([CH:14]=[C:15]1[C:20](=O)[CH2:19][CH2:18][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:16]1)C.[OH-].[Na+]>O>[CH3:6][S:7][C:8]1[N:9]=[CH:14][C:15]2[CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:19][C:20]=2[N:10]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

生成物 1

HCID 22710609tert-Butyl 2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate収率 40%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

S-Methylisothiourea sulfate (16.44 g, 59.06 mmol, 1.5 eq.) and tert-butyl 3-((dimethylamino)-methylene)-4-oxopiperidine-1-carboxylate (10.0 g, 39.37 mmol, 1.0 eq.) were taken up in water (40 ml); 1 M NaOH solution (50 ml) was added and stirring was carried out for 1 hour at 80° C. After monitoring by TLC, the reaction mixture was diluted with water (100 ml) and extracted with DCM (2×150 ml). The combined org. phases were washed with sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 25% ethyl acetate in hexane). Yield: 40% (4.5 g, 16.01 mmol)

後処理

  1. extractionextracted with DCM (2×150 ml)
  2. washphases were washed with sat. NaCl solution (100 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography (silica gel, 25% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-e862b422b0474663ba1dd5449de8d4db
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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