2-Pyrrolidone → HCID 86618458, compound

HRID 2403363Notes

Reaction equation

HRID 2403363 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.[NH:18]1[CH2:22][CH2:21][CH2:20][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:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 66053N,N-DimethylethylenediamineHCID 595930614-(2-Chloro-6-iodothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618458HCID 86618458, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine (150 mg), 90 μL of 2-pyrrolidinone, 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 16 h. The reaction mixture was evaporated and the residue was diluted with ethyl acetate (60 mL), washed with brine (30 mL), dried over MgSO4, filtered and evaporated. The crude product was purified on reverse phase HPLC to give 53 mg of 1-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)pyrrolidin-2-one.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with ethyl acetate (60 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-add7bf90de9e4096b848bc2f5b6a6aac
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

Loading…