Potassium Phosphate, Tribasic → 3-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)oxazolidin-2-one

HRID 2098886Notes

Reaction equation

HRID 2098886 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9](I)=[CH:8][C:6]=2[N:7]=1.[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C)CCN>O1CCOCC1.[Cu](I)I>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([N:20]3[CH2:21][CH2:22][O:18][C:19]3=[O:23])=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66053N,N-DimethylethylenediamineHCID 739492-OxazolidinoneHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 866184593-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)oxazolidin-2-oneYield 34.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine (150 mg), 2-oxazolidinone (103 mg), potassium phosphate tribasic (250 mg), copper iodide (7 mg), 4 μL of N,N-dimethylethylenediamine in 2 mL of 1,4-dioxane was heated to 100° C. for 15 hr. The reaction mixture was evaporated and the residue was diluted with ethyl acetate (50 mL), washed with brine (30 mL), dried over MgSO4, filtered and evaporated. The crude product was purified on reverse phase HPLC to give 46 mg of 3-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl) oxazolidin-2-one.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with ethyl acetate (50 mL)
  3. washwashed with brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-5ce2710b47e14cfbbe6fbff1587aa63a
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…