Phosphorus oxychloride → (R)-1-(4-chloro-pyrimidin-2-yl)ethyl butyrate

HRID 2227847Notes

Reaction equation

HRID 2227847 reaction equation
[C:1]([O:6][C@@H:7]([C:9]1[NH:14][C:13](=O)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:18])=O>>[C:1]([O:6][C@@H:7]([C:9]1[N:14]=[C:13]([Cl:18])[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10910803HCID 10910803, compound

Product 1

HCID 10944226(R)-1-(4-chloro-pyrimidin-2-yl)ethyl butyrate

Procedure

(R)-2-(1-Butyryloxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Fourteen, 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 dichloromethane and saturated aqueous sodium carbonate. The layers were separated and the organic layer was washed once 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, 3.19 g (85%). 1H NMR (CDCl3, 300 MHz) δ0.98 (t, 3H), 1.54 (d, 3H), 1.67 (m, 2H), 2.48 (t, 2H), 5.68 (q, 1H), 6.36 (d, 1H), 8.21 (d, 1H); [α]D +27.6 (c 1.0, MeOH).

Workup

  1. customaccording to the method of Preparation Fourteen, 3.00 g, 16.5 mmol)
  2. customExcess phosphorus oxychloride was removed under vacuum
  3. customthe resulting oil was partitioned between dichloromethane and saturated aqueous sodium carbonate
  4. customThe layers were separated
  5. washthe organic layer was washed once 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-bdf583b8f7ce459caf36234c96cc3485
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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