Trifluoroacetic acid → HCID 59834656, compound

HRID 271622Notes

Reaction equation

HRID 271622 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]2[CH:11]=[C:10]([CH2:12][N:13]3[C:18](=[O:19])[CH2:17][N:16](C(O)=O)[CH2:15][C:14]3=[O:23])[N:9]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]=2[N:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][N:9]1[C:7]2[N:8]=[C:3]([C:1]#[N:2])[N:4]=[CH:5][C:6]=2[CH:11]=[C:10]1[CH2:12][N:13]1[C:14](=[O:23])[CH2:15][NH:16][CH2:17][C:18]1=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86597001HCID 86597001, compound

Product 1

HCID 59834656HCID 59834656, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.5 g (23.9 mmoles) of 4-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-3,5-dioxo-piperazine-1-carboxylic acid .tert.-butyl ester in 300 ml of CH2Cl2, 52 ml (675 mmoles) of TFA is added at 0° C. The reaction mixture is allowed to warm to ambient temperature and stirred for 6 hours. The reaction mixture is concentrated under reduced pressure, neutralized with sat.NaHCO3 and extracted with CH2Cl2. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: CH2CO2:AcOEt=1:3) give 7.18 g of desired 7-(2,2-dimethyl-propyl)-6-(2,6-dioxo-piperazin-1-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile in 88.5% yield.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. extractionNaHCO3 and extracted with CH2Cl2
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent: CH2CO2:AcOEt=1:3)

Sources & evidence

ORD record
ord-c83a73f3880a4b60a8bb54fbf8d0a639
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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