(Pyridin-4-yl)boronic acid → 2-Phenyl-5-(pyridin-4-ylmethyl)pyrimidine
Reaction equation
Br[CH2:2][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.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1>>[C:9]1([C:6]2[N:5]=[CH:4][C:3]([CH2:2][C:18]3[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=3)=[CH:8][N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
Procedure
Synthesized using compound 64a (102 mg, 0.41 mmol) and 4-pyridineboronic acid (76 mg, 0.61 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:2) as eluent. After flash chromatography the product was solved in ethyl acetate and a few drops of conc. HCl and water were added. After stirring for 30 minutes the phases were separated and water phase was neutralized with aqueous Na2CO3-solution (2M). After extraction with ethyl acetate and drying over MgSO4 the solvent was removed under vacuum. White solid. Yield: 57 mg, 56%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.98 (s, 2H), 7.10-7.16 (m, 2H), 7.46-7.53 (m, 3H), 8.41-8.46 (m, 2H), 8.54-8.60 (m, 2H), 8.64 (s, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=35.6, 123.8, 128.0, 128.5, 128.6, 129.6, 130.7, 137.1, 147.5, 150.2, 157.4, 163.4; (ESI): m/z=247.80 [M+H]+.
Workup
- customSynthesized
- customCrude product was purified by flash chromatography on silica-gel
- additiona mixture of hexane/ethyl acetate (1:2) as eluent
- additiona few drops of conc. HCl and water were added
- customwere separated
- extractionAfter extraction with ethyl acetate
- dry with materialdrying over MgSO4 the solvent
- customwas removed under vacuum
Sources & evidence
- ORD record
- ord-3d2c69a15ec8454d8b264107d16d5f0e
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394290B2
Reaction notes
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