Triethylamine → HCID 58641490, compound

HRID 28378Notes

Reaction equation

HRID 28378 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:13]1[NH:14][C:15](=[O:25])[C:16]([OH:24])=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1)([O:9][CH2:10][CH2:11]O)[CH2:7][Cl:8])(=[O:3])[CH3:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28].CCN(CC)CC>O1CCCC1>[C:1]([O:4][CH2:5][C:6]1([CH2:7][Cl:8])[C:13]2=[N:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:16]([O:24][S:27]([CH3:26])(=[O:29])=[O:28])[C:15](=[O:25])[N:14]2[CH2:11][CH2:10][O:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136013282HCID 136013282, compound

Product 1

HCID 58641490HCID 58641490, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 2-(3-acetoxy-1-chloro-2-(2-hydroxyethoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (2.322 g, 6.13 mmol) in tetrahydrofuran (100 mL) was treated with methane sulfonylchloride (2.11 g, 18.4 mmol) and Et3N (2.25 g, 22 mmol) and then heated (60° C., oil bath) for 3 hrs. Solvent was removed in-vacuo and the crude product was dissolved in ethyl acetate (100 mL), then washed with water (2×50 mL). The organic solution was dried (Na2SO4), filtered and concentrated in-vacuo to give the title compound as a viscous amber oil which was used immediately in the following reaction.

Workup

  1. customSolvent was removed in-vacuo
  2. dissolutionthe crude product was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-190fd5002d614639b1aa7fa8ddae6656
Source dataset
uspto-grants-2008_09
Patent number
US07419969B2

Reaction notes

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