Dimethylacetamide → 4-Bromo-5-ethyl-6-[4-(aminomethyl-2-pyridinyl)-1-piperidinyl]-pyrimidine

HRID 2358221노트

반응식

HRID 2358221 반응식
C([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])(C)C.Br[C:11]1[C:16]([CH2:17][CH3:18])=[C:15]([Br:19])[N:14]=[CH:13][N:12]=1.CC1[CH2:26][CH2:25][N:24](NC2C=CC=CN=2)[CH2:23][CH2:22]1.[C:34](=O)(O)[O-].[Na+].[CH3:39][N:40](C)C(=O)C>C(OCC)(=O)C.O>[Br:19][C:15]1[C:16]([CH2:17][CH3:18])=[C:11]([N:24]2[CH2:25][CH2:26][CH:9]([C:7]3[C:8]([CH2:39][NH2:40])=[CH:34][CH:6]=[CH:5][N:4]=3)[CH2:22][CH2:23]2)[N:12]=[CH:13][N:14]=1

참가 물질

8

반응물 5

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 204537582-(4-Methylpiperidinyl)aminopyridineHCID 578328944,6-Dibromo-5-ethyl-pyrimidine

생성물 1

HCID 866036064-Bromo-5-ethyl-6-[4-(aminomethyl-2-pyridinyl)-1-piperidinyl]-pyrimidine수율 84%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

1.8 ml of diisopropylethylamine is added to a mixture of 657 mg (2.47 mmoles) of 4,6-dibromo-5-ethyl-pyrimidine and 450 mg (2.35 mmoles) of 2-(4-methylpiperidinyl)aminopyridine in 55 ml of N,N-dimethylacetamide. This mixture is heated at 110° C. for 4 hours. Then the solvent is eliminated under reduced pressure (0.2 kPa) and the residue is taken up in a mixture of ethyl acetate, water and a saturated solution of sodium bicarbonate. The organic phase is decanted, dried over magnesium sulphate then condensed under reduced pressure (2 kPa). The brown oil obtained is chromatographed on alumina eluting with the following gradient: heptane-ethyl acetate 80-20 to 70-30. 747 mg (Yield=84%) of expected product is obtained in the form of a beige solid.

후처리

  1. customThe organic phase is decanted
  2. dry with materialdried over magnesium sulphate
  3. customcondensed under reduced pressure (2 kPa)
  4. customThe brown oil obtained
  5. customis chromatographed on alumina eluting with the following gradient

출처 및 근거

ORD 기록
ord-8d551b1ce3854d61b7b68768a9c3a53a
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763621B2

반응 노트

불러오는 중…