(Pyrimidin-5-yl)boronic acid → 5-((6-Phenylpyridin-3-yl)methyl)pyrimidine

HRID 1054113Notes

Reaction equation

HRID 1054113 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH: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]=[C:19](B(O)O)[CH:18]=[N:17][CH:16]=1>>[C:9]1([C:6]2[N:7]=[CH:8][C:3]([CH2:2][C:19]3[CH:20]=[N:15][CH:16]=[N:17][CH:18]=3)=[CH:4][CH:5]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 159459965-(Bromomethyl)-2-phenylpyridine

Product 1

HCID 573300795-((6-Phenylpyridin-3-yl)methyl)pyrimidine

Procedure

Synthesized using compound 61a (219 mg, 0.88 mmol) and pyrimidine-5-boronic acid (164 mg, 1.32 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:1) 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: 43 mg, 20%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.02 (s, 2H), 7.39-7.44 (m, 1H), 7.44-7.56 (m, 3H), 7.70 (dd, J=8.2, 0.9 Hz, 1H), 7.95-8.00 (m, 2H), 8.58-8.67 (m, 3H), 9.13 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=33.4, 120.5, 126.8, 128.8, 129.1, 132.2, 133.3, 136.9, 138.7, 149.7, 156.4, 156.9, 157.3; (ESI): m/z=247.83 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (1:1) as eluent
  4. additiona few drops of conc. HCl and water were added
  5. customwere separated
  6. extractionAfter extraction with ethyl acetate
  7. dry with materialdrying over MgSO4 the solvent
  8. customwas removed under vacuum

Sources & evidence

ORD record
ord-ee96099f4a3e48ccb2b1f8e99a2b2374
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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