1,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate → 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 1366711Notes

Reaction equation

HRID 1366711 reaction equation
[N:1]1[C:9]2[CH:8]=[N:7][CH:6]=[N:5][C:4]=2[N:3]([CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)[N:2]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[CH2:10][N:3]1[C:4]2[N:5]=[CH:6][N:7]=[CH:8][C:9]=2[N:1]=[N:2]1

Participants

4

Reactant 1

HCID 669363511,1-dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate

Product 1

HCID 669365273-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidineYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl (2S)-2-(3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-ylmethyl)-1-pyrrolidinecarboxylate (1.98 g, 6.54 mmol) was dissolved in a mixture of CH2Cl2 (10 mL) and TFA (2.5 mL) and allowed to stir at room temperature overnight. When the reaction was complete as determined by LCMS, the solution was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (5 mL) and washed with 1 N aq. NaOH (30 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide 3-[(2S)-2-pyrrolidinylmethyl]-3H-[1,2,3]triazolo[4,5-d]pyrimidine (758 mg, 57%). LCMS: (M+H)+: 205.1.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  3. washwashed with 1 N aq. NaOH (30 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f33368b545548d5873e31a30239eb78
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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