Ethylenediamine → HCID 69662159, compound

HRID 1792259Notes

Reaction equation

HRID 1792259 reaction equation
Cl[C:2]1[C:14]2[N:13]3[C:8]([C:9]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[CH3:23])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:5]=[C:4]([CH3:24])[N:3]=1.[CH2:25]([NH2:28])[CH2:26][NH2:27].CCOC(C)=O>CN1C(=O)CCC1>[NH2:27][CH2:26][CH2:25][NH:28][C:2]1[C:14]2[N:13]3[C:8]([C:9]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[CH3:23])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:5]=[C:4]([CH3:24])[N:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8857Ethyl AcetateHCID 86595016HCID 86595016, compound

Product 1

HCID 69662159HCID 69662159, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 4-chloro-2-methyl-9-(2,4,6-trimethylphenyl)pyrimidino[4,5-b]indolizine (0.3 g, 0.89 mmol), and ethylene diamine (0.6 mL, 8.93 mmol) in dry NMP (3 mL) at 100° C. for 14 h. Pour the cooled mixture onto water (30 mL) and extracte twice with EtOAc (30 mL). Wash the combined extracts with brine (30 mL), dry, and evaporate in vacuo. Purify by preparative TLC (20% MeOH in CH2Cl2 with 0.5% ammonium hydroxide) to obtain the title compound as a yellow oil.

Workup

  1. additionPour the cooled mixture onto water (30 mL)
  2. washWash the combined extracts with brine (30 mL)
  3. customdry
  4. customevaporate in vacuo
  5. customPurify by preparative TLC (20% MeOH in CH2Cl2 with 0.5% ammonium hydroxide)

Sources & evidence

ORD record
ord-9b776e6a19444b638cd2ea1c6264dace
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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