Phosphorus oxychloride → Ethyl-2-methoxymethyl-4-chloropyrimidine-5-acetate

HRID 481421Notes

Reaction equation

HRID 481421 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8](O)[C:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][N:5]=1.P(Cl)(Cl)([Cl:19])=O>>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:7]1[C:8]([Cl:19])=[N:9][C:4]([CH2:3][O:2][CH3:1])=[N:5][CH:6]=1)[CH3:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470733HCID 178470733, compound

Product 1

HCID 19066271Ethyl-2-methoxymethyl-4-chloropyrimidine-5-acetateYield 78%

Procedure

A mixture of the product of Step 1, above (0.01 mol) and phosphorous oxychloride (7 ml) was refluxed for 20 minutes. The excess phosphorous oxychloride was removed, the residue was quenched with ice water (15 ml) and the mixture was extracted with ethyl acetate (2×20 ml). The ethyl acetate layer was collected and washed with water (2×10 ml). The organic extract was collected, dried over MgSO4 and the dried portion was evaporated to obtain the title compound as an oil (78% yield).

Workup

  1. customThe excess phosphorous oxychloride was removed
  2. customthe residue was quenched with ice water (15 ml)
  3. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  4. customThe ethyl acetate layer was collected
  5. washwashed with water (2×10 ml)
  6. extractionThe organic extract
  7. customwas collected
  8. dry with materialdried over MgSO4
  9. customthe dried portion was evaporated

Sources & evidence

ORD record
ord-7d69c9c0cd244e8aa1776baa6ae8f9ea
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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