Water → (2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-e]pyrimidin-4-yl]amine

HRID 2121590Notes

Reaction equation

HRID 2121590 reaction equation
Cl[C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:23]([O:25][C:26]1[CH:37]=[CH:36][C:29]([CH2:30][CH2:31][NH:32][CH2:33][CH2:34][NH2:35])=[CH:28][C:27]=1[O:38][CH3:39])[CH3:24].O>CN1C(=O)CCC1>[CH2:23]([O:25][C:26]1[CH:37]=[CH:36][C:29]([CH2:30][CH2:31][NH:32][CH2:33][CH2:34][NH:35][C:2]2[C:3]3[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]([C:14]4[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=4[CH3:22])[C:4]=3[N:5]=[C:6]([CH3:8])[N:7]=2)=[CH:28][C:27]=1[O:38][CH3:39])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 154284084-Chloro-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidineHCID 22034119N-(4-Ethoxy-3-methoxy-phenethyl)-ethylenediamine

Product 1

HCID 22034130(2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-e]pyrimidin-4-yl]amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 4-chloro-2,5,6-trimethyl-7-(2,4,6-trimethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine (340 mg, 1.1 mmol) and N-(4-ethoxy-3-methoxy-phenethyl)-ethylenediamine in NMP (2 mL) for 14 h at 130° C. Pour into water (5 mL) and extract with EtOAc (2×10 mL). Dry the combined organic extracts over Na2SO4, filter, and concentrate under reduced pressure. Purify by preparative TLC, eluting with 10% MeOH in CH2Cl2. Dissolve the residue in a minimum amount of MeOH then add HCl in EtOAc (2 mL) and triturate with Et2O to obtain the title compound as a solid (HCl salt).

Workup

  1. extractionextract with EtOAc (2×10 mL)
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify by preparative TLC
  6. washeluting with 10% MeOH in CH2Cl2
  7. dissolutionDissolve the residue in a minimum amount of MeOH
  8. customadd HCl in EtOAc (2 mL) and triturate with Et2O

Sources & evidence

ORD record
ord-4eb75880a15e4ffeb18bb742db6cb6b4
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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