Diisopropylethylamine → HCID 68027129, compound

HRID 527896Notes

Reaction equation

HRID 527896 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[C:15]1[C:16]2[CH:23]=[CH:22][NH:21][C:17]=2[N:18]=[CH:19][N:20]=1.CCN(C(C)C)C(C)C>CCO>[N:18]1[C:17]2[NH:21][CH:22]=[CH:23][C:16]=2[C:15]([N:1]2[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 68027129HCID 68027129, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (R)-tert-butyl pyrrolidin-3-ylcarbamate (250 mg, 1.34 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (206 mg, 1.34 mmol) and DIPEA (0.35 mL, 2.01 mmol) in EtOH (3 mL) was stirred at reflux temperature for 16 hours. The volatiles were removed under reduced pressure. The residue was dissolved in EtOAc (15 mL), and filtered. The filtrate was washed with brine (3×5 mL), dried over anhydrous Na2SO4, and concentrated to give the title compound (360 mg, 88% yield). MS (m/z): 304 (M+H)+.

Workup

  1. temperatureat reflux temperature for 16 hours
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (15 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with brine (3×5 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2fd565c0a3ed4bcba5e64eb3d5575cdf
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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