Diisopropylethylamine → HCID 68029225, compound

HRID 527901Notes

Reaction equation

HRID 527901 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:19]1[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20]1.CCN(C(C)C)C(C)C>CCO>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([N:19]3[CH2:23][CH2:22][C@@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:20]3)[C:3]=2[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 467367974-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 68029225HCID 68029225, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (900 mg, 3.17 mmol), (R)-tert-butyl pyrrolidin-3-ylcarbamate (709 mg, 3.80 mmol) and DIPEA (618 mg, 4.75 mmol) in EtOH (20 mL) was stirred at refluxed temperature for 3 hours. The volatiles were removed under reduced pressure and the residue was dissolved in EtOAc (100 mL), washed with brine (3×10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the tile compound. MS (m/z): 434 (M+H)+.

Workup

  1. temperatureat refluxed temperature for 3 hours
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc (100 mL)
  4. washwashed with brine (3×10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the tile compound

Sources & evidence

ORD record
ord-1cbaaf5f372545c6b24423d5eee2e5b3
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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