Triethylamine → HCID 44122670, compound

HRID 1519160Notes

Reaction equation

HRID 1519160 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(#N)C.O>[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][CH2:10][NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:18])([CH3:16])[CH3:17].[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][CH2:10][NH:9][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 187201N-BOC-ethylenediamine

Product 2

HCID 44122670HCID 44122670, compoundYield 58%HCID 54775425HCID 54775425, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2,4-Dichloropyrimidine (1.0 g, 6.7 mmol), tert-butyl N-(2-aminoethyl)carbamate (1.06 mL, 6.71 mmol) and triethylamine (1.12 mL, 8.05 mmol) were partially dissolved in acetonitrile (22.5 mL). The mixture was stirred at room temperature for 14 hours before diluting with water and extracting with DCM. The DCM extract was dried over Na2SO4, filtered and concentrated to dryness. The crude mixture was purified by FCC to give tert-butyl-(2-((2-chloropyrimidin-4-yl)amino)ethyl)carbamate (1.07 g, 58%) and tert-butyl-(2-((4-chloropyrimidin-2-yl)amino)ethyl)carbamate (280 mg, 15%).

Workup

  1. extractionextracting with DCM
  2. extractionThe DCM extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude mixture was purified by FCC

Sources & evidence

ORD record
ord-3c349d7c3bf249338a47556fad1a6e60
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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