Trifluoroacetic acid → 6-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

HRID 624589Notes

Reaction equation

HRID 624589 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:17]2[C:12]([N:13]([CH3:28])[C:14](=[O:27])[N:15]([CH3:26])[C:16]2=[O:25])=[CH:11]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][N:10]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:17]2[C:12]([N:13]([CH3:28])[C:14](=[O:27])[N:15]([CH3:26])[C:16]2=[O:25])=[CH:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722910[2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 867228796-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-ethyl]-carbamic acid tert-butyl ester (step 4) (1.11 g, 2.79 mmol) was dissolved in DCM (10 mL) and treated with trifluoroacetic acid (2.1 mL, 25.1 mmol). The reaction was stirred at RT for 4 h. The reaction was quenched by pouring into stirring 2M NaOH and further NaOH added until alkaline to pH paper. The layers were separated and the aqueous phase extracted with DCM (3×75 mL). The combined organic phases were washed with water (100 mL), brine (75 mL) and passed through a hydrophobic frit. The solvent was removed under reduced pressure, affording the title compound as an off-white solid.

Workup

  1. customThe reaction was quenched
  2. additionby pouring
  3. stirringinto stirring 2M NaOH and further NaOH
  4. additionadded until alkaline
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with DCM (3×75 mL)
  7. washThe combined organic phases were washed with water (100 mL), brine (75 mL)
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b7afa1bc34474e4d8c4abbcb9e28f373
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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