Water → HCID 58394344, compound

HRID 2189201Notes

Reaction equation

HRID 2189201 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.[Cl:21][C:22]1[N:27]=[C:26](Cl)[CH:25]=[CH:24][N:23]=1.O>CC(N(C)C)=O>[Cl:21][C:22]1[N:27]=[C:26]([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)[CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 58394344HCID 58394344, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(S)-(−)-1-Boc-3-aminopyrrolidine (0.375 g, 2.014 mmol) and triethylamine (0.561 mL, 4.028 mmol) were added to a solution of 2,4-dichloropyrimidine (0.300 g, 2.014 mmol) in DMA (12 mL) at 0° C. After 24 hours at room temperature, water (150 mL) was added and the aqueous phase was extracted with ethyl acetate (3×40 mL). The combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by silica gel chromatography (5% methanol in dichloromethane) to give the title compound as an oil (0.540 g, 90%).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b77dd207c7d445b88de1e859af659937
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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