Imidazole → (1H-imidazol-1-yl)methyl-2-phenylpyrimidine

HRID 1054109Notes

Reaction equation

HRID 1054109 reaction equation
BrC[C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.[C:20]([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:15]1([CH2:20][C:8]2[CH:3]=[CH:4][N:5]=[C:6]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:7]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 218300465-(Bromomethyl)-2-phenylpyrimidine

Product 1

HCID 131736320(1H-imidazol-1-yl)methyl-2-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Synthesized using compound 64a (70 mg, 0.28 mmol), imidazole (76 mg, 1.12 mmol) and K2CO3 (195 mg, 1.41 mmol) in acetonitrile according to Method B. Crude product was purified by flash chromatography on silica-gel using ethyl acetate as eluent. After flash chromatography the product was recrystallized in ethyl acetate. Light yellow solid. Yield: 62 mg, 94%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.17 (s, 2H), 6.94 (t, J=1.3 Hz, 1H), 7.15 (t, J=1.1 Hz, 1H), 7.47-7.54 (m, 3H), 7.61 (s, 1H), 8.41-8.46 (m, 2H), 8.63 (s, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=46.0, 118.8, 127.0, 128.2, 128.7, 130.7, 131.1, 136.8, 137.2, 156.2, 164.8; (ESI): m/z=236.92 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. customAfter flash chromatography the product was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-253dca3d93fe4e81b9f7b57a3a4c0348
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…