Diisopropylethylamine → HCID 22309469, compound

HRID 404798Notes

Reaction equation

HRID 404798 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][N:5]=[CH:4][N:3]=1.[NH2:9][CH:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH:9][CH:10]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 115500374,5-dichloropyrimidine

Product 1

HCID 22309469HCID 22309469, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4,5-dichloropyrimidine (0.6 g, 4.02 mmol), 3-amino-Boc-pyrrolidine (0.5 g, 2.6 mmol) and DIPEA (1.73 g, 13.3 mmol) in n-butanol (5.0 mL) was heated in a pressure tube (120° C., 12 h). It was cooled, quenched with water (10 mL), and was extracted with EtOAc (2×25 mL). The combined EtOAc extract was washed with water (5 mL), brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure to afford tert-butyl 3-(6-chloropyrimidin-4-ylamino)pyrrolidine-1-carboxylate (0.4 g, 50%) as a yellow solid.

Workup

  1. temperatureIt was cooled
  2. customquenched with water (10 mL)
  3. extractionwas extracted with EtOAc (2×25 mL)
  4. extractionThe combined EtOAc extract
  5. washwas washed with water (5 mL), brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4412a9725ad748c3b784e0e319c6bdf8
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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