N-Methylcyclohexylamine → Methyl 2-(2-(cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

HRID 1399582노트

반응식

HRID 1399582 반응식
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.[CH3:24][NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1.C(=O)([O-])O.[Na+]>[CH:26]1([N:25]([CH3:24])[C:2]2[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:3]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

참가 물질

5

반응물 2

HCID 7514N-MethylcyclohexylamineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

생성물 1

HCID 50997699Methyl 2-(2-(cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate수율 49.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
100 °C

실험 절차

A mixture of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.30 mmol) and N-methylcyclohexanamine (0.158 mL; 1.202 mmol) in THF (1 mL) was placed in a sealed tube and heated at 100° C. for 18 h. The reaction mixture was diluted with a saturated sodium hydrogen carbonate solution and extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 61 mg (49%) of the title compound.

후처리

  1. customwas placed in a sealed tube
  2. extractionextracted twice with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane

출처 및 근거

ORD 기록
ord-8cc3e8cd481c49a7a733acc7782bd9a5
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906906B2

반응 노트

불러오는 중…