Triethylamine → HCID 76284847, compound

HRID 624574Notes

Reaction equation

HRID 624574 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:7](O)[CH2:8][O:9][CH2:10][CH2:11][N:12]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:14]([N:15]([CH3:30])[C:16](=[O:29])[N:17]([CH3:28])[C:18]3=[O:27])=[CH:13]2)[S:5][CH:6]=1.C(N(CC)CC)C.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[CH2:8][O:9][CH2:10][CH2:11][N:12]3[C:20]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[C:19]4[C:18](=[O:27])[N:17]([CH3:28])[C:16](=[O:29])[N:15]([CH3:30])[C:14]4=[C:13]23)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471Triethylamine3×HCID 67749Trifluoromethanesulfonic anhydride3×HCID 86722898HCID 86722898, compound

Product 1

HCID 76284847HCID 76284847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(2-(2-(4-Chlorothiazol-2-yl)-2-hydroxyethoxy)ethyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (300 mg, 0.651 mmol), and triethylamine (0.272 mL, 1.953 mmol) were dissolved in DCM (10 mL) and Tf2O (0.165 mL, 0.976 mmol) was added in a single portion. The mixture was stirred at room temp. for 15 mins and further triethylamine (0.272 mL, 1.953 mmol) and Tf2O (0.165 mL, 0.976 mmol) were added. After 45 mins, further triethylamine (0.272 mL, 1.953 mmol) and Tf2O (0.165 mL, 0.976 mmol) were added. After stirring for a further 45 mins, the reaction was quenched with sat. NaHCO3(aq) and extracted with DCM (3×). The combined organic phases were passed through a hydrophobic frit and evaporated under vacuum. The residue was redissolved in DCM and evaporated onto silica. The silica was deposited onto a 10 g silica cartridge and the system gradient-eluted from 10-80% EtOAc/hexane. The product fractions were combined and evaporated. The resulting residue was triturated with DCM/Et2O/hexane and the precipitate collected by filtration to afford the title compound as a pale yellow solid;

Workup

  1. waitAfter 45 mins
  2. stirringAfter stirring for a further 45 mins
  3. customthe reaction was quenched with sat. NaHCO3(aq)
  4. extractionextracted with DCM (3×)
  5. customevaporated under vacuum
  6. dissolutionThe residue was redissolved in DCM
  7. customevaporated onto silica
  8. washthe system gradient-eluted from 10-80% EtOAc/hexane
  9. customevaporated
  10. customThe resulting residue was triturated with DCM/Et2O/hexane
  11. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-a4bfef394595464bb90ad0afa41a1c23
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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