Chloromethyl ethyl ether → HCID 10608588, compound

HRID 1451208Notes

Reaction equation

HRID 1451208 reaction equation
[CH:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)([CH3:3])[CH3:2].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.Cl[CH2:25][O:26][CH2:27][CH3:28]>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:27]([O:26][CH2:25][N:8]1[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:11])[NH:6][C:7]1=[O:10])[CH3:28]

Participants

6

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 985755-IsopropyluracilHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 10608588HCID 10608588, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-isopropyluracil (18 g) in dichloromethane (230 ml) was added bis-trimethylsilylacetamide (60.7 ml) and the mixture stirred for 1 hr at room temperature. To the solution were added tetra-n-butylammonium iodide (0.46 g) and chloromethylethyl ether (10.7 ml) at room temperature and the mixture stirred for 1.5 hr. The resultant mixture was washed and partitioned with cooled water (50 ml) (×2). The organic layer was concentrated under reduced pressure. The residue was crystallized at room temperature from n-heptane (100 ml) to yield 1-ethoxymethyl-5-isopropyluracil (22.2 g). M.p., 78.4° C.

Workup

  1. stirringthe mixture stirred for 1.5 hr
  2. washThe resultant mixture was washed
  3. custompartitioned with cooled water (50 ml) (×2)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was crystallized at room temperature from n-heptane (100 ml)

Sources & evidence

ORD record
ord-077f362b9585488b8a56d5f415226e02
Source dataset
uspto-grants-1997_02
Patent number
US05604209

Reaction notes

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