(S)-1-[3-(4-Methoxy-benzyl)-5-(2,2,2-trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol → HCID 178521640, compound

HRID 2179103Notes

Reaction equation

HRID 2179103 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[C:14]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:15]=[C:16]([N:17]4[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18]4)[C:11]=3[N:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[F:27][C:25]([F:26])([F:28])[CH2:24][O:23][C:14]1[N:15]=[C:16]([N:17]2[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18]2)[C:11]2[N:10]=[N:9][NH:8][C:12]=2[N:13]=1

Participants

3

Reactant 1

HCID 89586559(S)-1-[3-(4-Methoxy-benzyl)-5-(2,2,2-trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

Product 1

HCID 178521640HCID 178521640, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-1-[3-(4-Methoxy-benzyl)-5-(2,2,2-trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 109, d) in 4.57 mL TFA was heated to 80° C. over night and evaporated. The residue was treated with 1M NaOH and washed with EtOAc. The combined organic layer was evaporated to yield the crude title compound which was used in the consecutive step without further purification. MS (m/e): 305.2 (MH+).

Workup

  1. customevaporated
  2. additionThe residue was treated with 1M NaOH
  3. washwashed with EtOAc
  4. customThe combined organic layer was evaporated

Sources & evidence

ORD record
ord-adaa42725f9c47efab709dec1c20e504
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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