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

HRID 2227845Notes

Reaction equation

HRID 2227845 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) δ1.56 (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-8e9eaa0f8e9e4881a4f048eac819433e
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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