Sodium Carbonate → 7-[(E)-2-(4-Chlorophenyl)vinyl]-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1642414Notes

Reaction equation

HRID 1642414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]3[S:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2I)=[CH:4][CH:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]3[S:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66753972HCID 66753972, compound

Product 1

HCID 444679427-[(E)-2-(4-Chlorophenyl)vinyl]-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 5,932.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of Intermediate 1 (100 mg, 0.231 mmol) in toluene (20 ml) and ethanol (10 ml) was added phenylboronic acid (33 mg, 0.276 mmol) and Pd[(C6H5)3P]4 (26 mg, 0.023 mmol) in) followed by sodium carbonate (Na2CO3) (48 mg, 0.461 mmol) in water (10 ml). The reaction mixture was heated to reflux for 12 h under nitrogen. The reaction mixture was allowed to cool to room temperature. The residue obtained after evaporation was partitioned between ethyl acetate (500 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried (Na2SO4) and concentrated to afford a crude product which was purified by silica gel column chromatography using 10% ethyl acetate in chloroform to give 5 g of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.19 (s, 3H), 6.85 (d, J=4.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 3H), 7.77 (m, 4H), 7.88 (d, J=7.8 Hz, 1H), 8.02 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 265.31 (M−H)−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h under nitrogen
  3. customThe residue obtained
  4. customafter evaporation
  5. customwas partitioned between ethyl acetate (500 ml) and water (100 ml)
  6. washThe organic layer was washed with brine (100 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto afford a crude product which
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-de6f68e7d57443469d6840c2c014e217
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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