Triethylamine → (R)-1-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl acetate

HRID 586200Notes

Reaction equation

HRID 586200 reaction equation
[C:1]([O:4][C@@H:5]([C:7]1[NH:12][C:11](=[O:13])[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[C:1]([O:4][C@@H:5]([C:7]1[N:12]=[C:11]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11105982(R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one

Product 1

HCID 54125954(R)-1-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of (R)-2-(1-acetoxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Thirteen, 2.58 g, 14.2 mmol) and triethylamine (1.43 g, 14.2 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (1.63 g, 14.2 mmol) dropwise and stirred for 1 h. The mixture was washed successively with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate and filtered. The filtrate was evaporated to give the title compound as an oil, 3.15 g (85%). 1H NMR (CDCl3, 300 MHz) δ 1.56 (d, 3H), 2.18 (s, 3H), 3.82 (s, 3H), 5.56 (q, 1H), 6.38 (d, 1H), 8.24 (d, 1H); MS (CI) 261 (MH+); [α]D+53.8 (c 1.1, MeOH).

Workup

  1. washThe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b7c3262837994f76bca66c2b484f1e6d
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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