1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-((Benzyloxy)methyl)-6-bromo-1,5-dimethylpyrimidine-2,4(1h,3h)-dione

HRID 2281933Notes

Reaction equation

HRID 2281933 reaction equation
N12CCCN=C1CCCCC2.[Br:12][C:13]1[N:18]([CH3:19])[C:17](=[O:20])[NH:16][C:15](=[O:21])[C:14]=1[CH3:22].Cl[CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH2:26]([O:25][CH2:24][N:16]1[C:15](=[O:21])[C:14]([CH3:22])=[C:13]([Br:12])[N:18]([CH3:19])[C:17]1=[O:20])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137983Benzyl chloromethyl etherHCID 901161616-Bromo-1,5-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 1177735843-((Benzyloxy)methyl)-6-bromo-1,5-dimethylpyrimidine-2,4(1h,3h)-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (6.00 mL, 40.2 mmol) was added to a suspension of C2 (8.00 g, 36.5 mmol) and benzyl chloromethyl ether (95%, 5.86 mL, 40.2 mmol) in acetonitrile (100 mL). After 90 hours at room temperature, the reaction mixture was concentrated in vacuo, diluted with water, and extracted several times with ethyl acetate. The combined organic layers were washed sequentially with water and with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 10% to 25% ethyl acetate in heptane) afforded the product as a white solid. Yield: 10.1 g, 29.8 mmol, 82%. 1H NMR (400 MHz, CDCl3) δ 7.24-7.39 (m, 5H), 5.52 (s, 2H), 4.71 (s, 2H), 3.63 (s, 3H), 2.11 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted several times with ethyl acetate
  4. washThe combined organic layers were washed sequentially with water and with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39f8d5022fe94d34bb77e6d47a9b3d6f
Source dataset
uspto-grants-2015_09
Patent number
US09139561B2

Reaction notes

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