Piperazine → HCID 20689199, compound

HRID 1597194Notes

Reaction equation

HRID 1597194 reaction equation
[C:1]([O:6][C@H:7]([C:9]1[N:14]=[C:13](O)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.S(Cl)(C)(=O)=O.[NH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(Cl)Cl>[C:1]([O:6][C@H:7]([C:9]1[N:14]=[C:13]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:12]=[CH:11][N:10]=1)[CH3:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178454726HCID 178454726, compound

Product 1

HCID 20689199HCID 20689199, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 1-(S)-(4-hydroxy-pyrimidin-2-yl)-ethyl butyrate (0.42 g, 2.0 mmol) and triethylamine (0.20 g, 2.2 mmol) in methylene chloride (10 mL) was added mesyl chloride (0.25 g, 2.1 mmol) dropwise and stirred for 1.5 h. The mixture was washed successively with saturated bicarbonate and water, and the organic layer dried over anhydrous magnesium sulfate. It was, filtered and evaporated to give 1-(S)-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl as an oil. The oil was dissolved in tetahydrofuran (10 mL), and to the solution was added piperazine (0.69 g, 8.0 mmol) and stirred at ambient temperature for 4 hr. The mixture was filtered and the filtrate was concentrated to obtain a crude product which was purified by flash chromatography (9:1 methylene chloride/methanol) to give the title compound as a oil 0.50 g (90%). 1H NMR (CDCl3, 300 MHz) δ0.95 (t, 3H), 1.51 (d, 3H) 1.68 (m, 2), 2.66 (t, 2H), 2.83 (m, 4H), 3.63 (m, 4H), 5.54 (q, 1H), 6.38 (d, 1H), 8.24 (d, 1H); MS (Cl) 251 (MH+).

Workup

  1. washThe mixture was washed successively with saturated bicarbonate and water
  2. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give 1-(S)-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl as an oil
  6. dissolutionThe oil was dissolved in tetahydrofuran (10 mL)
  7. stirringstirred at ambient temperature for 4 hr
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated
  10. customto obtain a crude product which
  11. customwas purified by flash chromatography (9:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-e21b319f341342b18579b9aa89602cda
Source dataset
uspto-grants-2001_09
Patent number
US06294538B1

Reaction notes

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