Sodium Carbonate → (E)-5-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H,3H-pyrimidine-2,4-dione

HRID 890100Notes

Reaction equation

HRID 890100 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[O:16]=[C:17]1[NH:22][C:21](=[O:23])[C:20]([CH:24]=O)=[CH:19][NH:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH:10]1[CH2:11][CH2:12][N:13]([CH2:24][C:20]2[C:21](=[O:23])[NH:22][C:17](=[O:16])[NH:18][CH:19]=2)[CH2:14][CH2:15]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 3045905-FormyluracilHCID 5049666Sodium triacetoxyborohydride2×HCID 22248269(E)-4-[2-(2-fluorophenyl)vinyl]piperidine

Product 1

HCID 22248445(E)-5-[4-[2-(2-Fluorophenyl)vinyl]piperidino]methyl-1H,3H-pyrimidine-2,4-dioneYield 56.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 100 mg of (E)-4-[2-(2-fluorophenyl)vinyl]piperidine in 3 ml of tetrahydrofuran, 116 mg of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxaldehyde, 0.05 ml of acetic acid and 198 mg of sodium triacetoxyborohydride were added while stirring, and the stirring was continued for 20 hours at room temperature. An additional 200 mg of sodium triacetoxyborohydride was then added and the mixture was stirred overnight at room temperature. Aqueous sodium carbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: tetrahydrofuran/methanol). Ethyl acetate was added and the mixture was filtered to obtain the title compound (90 mg, 38% yield).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred overnight at room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (solvent: tetrahydrofuran/methanol)
  7. additionEthyl acetate was added
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-3b463f3732444c61ab2155417ae605e2
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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