Triethylamine → HCID 58394392, compound

HRID 2189198Notes

Reaction equation

HRID 2189198 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[Br:21][C:22]1[C:23](Cl)=[N:24][C:25]([Cl:28])=[N:26][CH:27]=1>O1CCOCC1>[Br:21][C:22]1[C:23]([NH:13][C@H:10]2[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)=[N:24][C:25]([Cl:28])=[N:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 58394392HCID 58394392, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-(−)-1-Boc-3-aminopyrrolidine (0.817 g, 4.39 mmol) and triethylamine (1.22 mL, 8.78 mmol) were added to a solution of 5-bromo-2,4-dichloropyrimidine (1.00 g, 4.39 mmol) in dioxane (22 mL) at 10° C. After 20 hours at room temperature, the solution was concentrated, dissolved in CH2Cl2 (50 mL) and washed with 2 M aqueous K2CO3 (50 mL). The aqueous layer was further extracted with CH2Cl2 (50 mL). The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by silica gel chromatography (50% ethyl acetate/hexanes) to give the title compound as an oil (1.106 g, 67%).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutiondissolved in CH2Cl2 (50 mL)
  3. washwashed with 2 M aqueous K2CO3 (50 mL)
  4. extractionThe aqueous layer was further extracted with CH2Cl2 (50 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8279accf3d5646119b55762c279378f0
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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