Trifluoroacetic acid → 2-(Methylthio)-6,7-dihydro-5H-pyrrolo[3,4-D]pyrimidine

HRID 338725Notes

Reaction equation

HRID 338725 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:7]=2[N:8]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18442822Tert-butyl 2-(methylthio)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

Product 1

HCID 670658482-(Methylthio)-6,7-dihydro-5H-pyrrolo[3,4-D]pyrimidineYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 2-(methylthio)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (1.43 g, 5.36 mmol) in dichloromethane (10 mL) was added a solution of trifluoroacetic acid (4.0 mL, 52 mmol) in dichloromethane (5 mL). The solution was stirred at room temperature for 3 hours. The dichloromethane was removed in vacuo. The residue was dissolved in water, treated with 5M sodium hydroxide to pH=14 and extracted with dichloromethane (5×10 mL). The organic layer was dried (MgSO4) filtered and evaporated to give the title compound (870 mg, 97%).

Workup

  1. customThe dichloromethane was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. additiontreated with 5M sodium hydroxide to pH=14
  4. extractionextracted with dichloromethane (5×10 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eda2a1f15bb8480c92ca6a0866039a25
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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