[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+].N1C=CC=NC=1>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]=1Next, into a reaction container were put 2.99 g of exo-2-bromonorbornane, 0.50 g of magnesium, and 10 mL of tetrahydrofuran (THF), and this reaction container was heated by irradiation with microwaves (2.45 GHz, 100 W) for 10 minutes so that Grignard reagent was prepared. 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, 30 mg of [1,2-bis(diphenylphosphino)ethane]nickel(II) dichloride (abbreviation: Ni(dppe)Cl2) was also added, then the temperature of the mixture was increased to room temperature. To this reaction solution was added an aqueous solution of ammonium chloride, 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 Hnbppm, which is the objective substance and a pyrimidine derivative (yellow oily substance, 43% in yield). A synthetic scheme of Step 2 is shown by a following (b-2).
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