Ammonium Chloride → 4-(2-Norbornyl)-6-phenylpyrimidine

HRID 1499032

反応式

HRID 1499032 の反応式
[CH2:1]1[CH:5]2[CH2:6][CH:7](Br)[CH:3]([CH2:4]2)[CH2:2]1.[Mg].Cl[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl.O1CCCC1>[CH:3]12[CH2:4][CH:5]([CH2:1][CH2:2]1)[CH2:6][CH:7]2[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=[CH:13][N:12]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 982322-Norbornyl bromideHCID 5934294-Chloro-6-phenylpyrimidineHCID 5462224Magnesium

生成物 1

HCID 683150824-(2-Norbornyl)-6-phenylpyrimidine

試薬・触媒・溶媒 2

HCID 2734542[1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

Into a reaction container, 2.99 g of exo-2-bromonorbornane, 0.50 g of magnesium, and 10 mL of tetrahydrofuran (THF) were put, and this reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes so that the Grignard reagent was prepared. Then, 5.02 g of 4-chloro-6-phenylpyrimidine obtained in Step 1 and 30 mL of THF were mixed, and while the mixture was being stirred at −15° C., the obtained Grignard reagent was added thereto. Further, 30 mg of [1,2-bis(diphenylphosphino)ethane]nickel(II) dichloride (abbreviation: Ni(dppe)Cl2) was also added, and the temperature of the mixture was increased to room temperature. An aqueous solution of ammonium chloride was added to this reaction solution, and an organic layer was extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by flash column chromatography (silica gel) using a mixed solvent of hexane and ethyl acetate as a developing solvent in a volume ratio of 5:1, to give the objective pyrimidine derivative Hnbppm (yellow oily substance, 43% in yield). The synthesis scheme of Step 2 is shown by (b-1).

後処理

  1. customwas prepared
  2. temperaturethe temperature of the mixture was increased to room temperature
  3. extractionan organic layer was extracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried with magnesium sulfate
  5. filtrationAfter the drying, the solution was filtered
  6. distillationThe solvent of this solution was distilled off
  7. customthe obtained residue was purified by flash column chromatography (silica gel)
  8. customto give

出典と根拠

ORDレコード
ord-268ac594c4e54deaa7cfed20d5519f27
出典データセット
uspto-grants-2015_12
特許番号
US09200022B2

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