Phosphorus oxychloride → (R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate

HRID 586199Notes

Reaction equation

HRID 586199 reaction equation
[C:1]([O:4][C@@H:5]([C:7]1[NH:12][C:11](=O)[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[C:1]([O:4][C@@H:5]([C:7]1[N:12]=[C:11]([Cl:16])[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11105982(R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one

Product 1

HCID 54154993(R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate

Procedure

(R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Thirteen, 3.00 g, 16.5 mmol) was added to phosphorus oxychloride (10 mL) at ambient temperature and stirred for 3 h. Excess phosphorus oxychloride was removed under vacuum and the resulting oil was partitioned between chloroform and saturated aqueous sodium carbonate. The layers were separated and the organic layer was washed twice with water, once with saturated aqueous sodium chloride and dried over magnesium sulfate and filtered. The filtrate was evaporated to give the title compound as an orange oil, 2.88 g (87%). 1H NMR (CDCl3, 300 MHz) δ 1.56 (d, 3H), 2.18 (s, 3H), 5.68 (q, 1H), 6.32 (d, 1H), 8.21 (d, 1H); MS (CI) 201, 203 (MH+); [α]D+27.6 (c 1.0, MeOH).

Workup

  1. customaccording to the method of Preparation Thirteen, 3.00 g, 16.5 mmol)
  2. customExcess phosphorus oxychloride was removed under vacuum
  3. customthe resulting oil was partitioned between chloroform and saturated aqueous sodium carbonate
  4. customThe layers were separated
  5. washthe organic layer was washed twice with water, once with saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d8c382f49bfb4e3eb3b588671b88f315
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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