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

HRID 1193353노트

반응식

HRID 1193353 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-e862b422b0474663ba1dd5449de8d4db
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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