Water → HCID 22285237, compound

HRID 1274983Notes

Reaction equation

HRID 1274983 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1.O>C(O)CC>[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 22285237HCID 22285237, compoundYield 134.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

N-(Boc)ethylenediamine (0.80 g, 5.0 mmol) (Syn. Commun. 1990, 20, 255-264) was dissolved in 1-propanol (12 mL) and treated with K2CO3 (1.2 g, 9.0 mmol), followed by 2-chloropyrimidine (0.91 g, 8.0 mmol), and the mixture was heated to reflux for 24 h. The reaction mixture was poured into H2O (30 mL) and extracted with EtOAc (3×30 mL). The combined organic fractions were dried (MgSO4) and concentrated to give the title compound as a yellow solid (1.6 g): MS (ES) m/e 238.9 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a5b81710c114eb19f04d14e9c25f1a1
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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