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

HRID 2358221ノート

反応式

HRID 2358221 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8d551b1ce3854d61b7b68768a9c3a53a
出典データセット
uspto-grants-2010_07
特許番号
US07763621B2

反応ノート

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