Ethylenediamine → HCID 69662159, compound

HRID 2121587Notes

Reaction equation

HRID 2121587 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]>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

4

Reactant 2

HCID 3301EthylenediamineHCID 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 extracted 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. extractionextracted twice with EtOAc (30 mL)
  3. washWash the combined extracts with brine (30 mL)
  4. customdry
  5. customevaporate in vacuo
  6. customPurify by preparative TLC (20% MeOH in CH2Cl2 with 0.5% ammonium hydroxide)

Sources & evidence

ORD record
ord-d26bc070f85e402bb463adac773113e8
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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