Trifluoroacetic acid → 3-[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]pentanedinitrile

HRID 40909Notes

Reaction equation

HRID 40909 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[S:20][C:19]([CH:21]([CH2:25][C:26]#[N:27])[CH2:22][C:23]#[N:24])=[N:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:12]1[C:11]2[NH:7][CH:8]=[CH:9][C:10]=2[C:15]([C:16]2[S:20][C:19]([CH:21]([CH2:25][C:26]#[N:27])[CH2:22][C:23]#[N:24])=[N:18][CH:17]=2)=[N:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574776413-[5-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]pentanedinitrile

Product 1

HCID 177549033-[5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]pentanedinitrileYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[5-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,3-thiazol-2-yl]pentanedinitrile (14 mg, 0.033 mmol) in DCM (3 mL) containing TFA (0.6 mL) was stirred for 4 hours. The mixture was then concentrated and the residue was redissolved in methanol (2 mL) to which ethylenediamine (0.4 mL) was then added. After 1 hour reaction time, the product was purified by preparative-HPLC/MS (C18 eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to afford the desired product (6 mg, 62%).

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue was redissolved in methanol (2 mL) to which ethylenediamine (0.4 mL)
  3. additionwas then added
  4. customAfter 1 hour reaction time
  5. customthe product was purified by preparative-HPLC/MS (C18
  6. washeluting with a gradient of ACN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-9d1a17f22d074314ae610e91d4152257
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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