Ammonium Chloride → 5-Methyl-4-(2-norbornyl)-6-phenylpyrimidine

HRID 1499034노트

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HRID 1499034 반응식
[CH2:1]1[CH:5]2[CH2:6][CH:7](Br)[CH:3]([CH2:4]2)[CH2:2]1.[Mg].Cl[C:11]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>C1COCC1>[CH3:17][C:16]1[C:11]([CH:7]2[CH2:6][CH:5]3[CH2:4][CH:3]2[CH2:2][CH2:1]3)=[N:12][CH:13]=[N:14][C:15]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 982322-Norbornyl bromideHCID 5462224MagnesiumHCID 59762769HCID 59762769, 화합물

생성물 1

HCID 708721515-Methyl-4-(2-norbornyl)-6-phenylpyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

Into a reaction container, 4.2 g of exo-2-bromonorbornane, 0.70 g of magnesium, and 12 mL of 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, 2.3 g of 4-chloro-5-methyl-6-phenylpyrimidine obtained in Step 1 and 20 mL of THF were mixed, and while the mixture was being stirred at −20° C., the obtained Grignard reagent was added thereto. Further, 40 mg of 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 dichloromethane and ethyl acetate as a developing solvent in a volume ratio of 9:1, to give the objective pyrimidine derivative Hnbmppm (yellow oily substance, 17% in yield). Note that the irradiation with microwaves was performed using a microwave synthesis system (Discover, manufactured by CEM Corporation). The synthesis scheme of Step 2 is shown by (b-3).

후처리

  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

출처 및 근거

ORD 기록
ord-b4024ecf22b9478481f52ac16d72de38
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200022B2

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