Potassium Phosphate, Tribasic → 2-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-ylamino)ethanol

HRID 2262138Notes

Reaction equation

HRID 2262138 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]C1=O.[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]([NH:20][CH2:21][CH2:22][OH:18])=[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 866184112-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-ylamino)ethanol

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-6-iodo-4-morpholinothieno[3,2-d]pyrimidine 19 (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, dried over MgSO4, filtered and evaporated. The crude product was purified on reverse phase HPLC to give 2-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-ylamino)ethanol as a by-product.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with ethyl acetate (50 mL)
  3. washwashed with brine
  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-f9378585f6ca4a6796c7e06bcf354e7c
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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