Triethylamine → Benzyl 4-(4-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)piperidin-1-carboxylate

HRID 20233

반응식

HRID 20233 반응식
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)=[C:2]=[O:3].Br.Br[CH2:22][CH2:23][CH:24]([NH2:26])[CH3:25].C(N(CC)CC)C.CC(C)([O-])C.[K+]>C(#N)C.C1COCC1>[CH3:25][CH:24]1[CH2:23][CH2:22][N:1]([CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:6][CH2:5]2)[C:2](=[O:3])[NH:26]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylateHCID 135559884-Bromobutan-2-amine hydrobromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 68420479Benzyl 4-(4-methyl-2-oxotetrahydropyrimidin-1(2H)-yl)piperidin-1-carboxylate수율 62%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A solution of benzyl 4-isocyanatopiperidin-1-carboxylate (0.26 g) in acetonitrile (10 mL) was added to a solution of 4-bromobutan-2-amine hydrobromide (0.17 g) and triethylamine (0.10 g) in acetonitrile (10 mL), followed by stirring at room temperature for one hour. Potassium tert-butoxide (0.29 g) and THF (20 mL) were added thereto, and the mixture was further stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1) to obtain the title compound (0.15 g, 45%) as a light brown solid.

후처리

  1. stirringthe mixture was further stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1)

출처 및 근거

ORD 기록
ord-dd0ca6057de441808d4ef09f4c6f81e1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745623B2

연결된 노트

불러오는 중…