1,3-Propanediamine → N-[3-{N-(3-amino-propyl)-aminocarbonyl}-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

HRID 2162

Reaction equation

HRID 2162 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=O.[NH2:29][CH2:30][CH2:31][CH2:32][NH2:33]>C(OCC)(=O)C>[NH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:19]=3)[CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 19689556N-[3-methoxycarbonylphenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

Product 1

HCID 19689550N-[3-{N-(3-amino-propyl)-aminocarbonyl}-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

100 mg (0.26 mmol) of N-[3-methoxycarbonyl-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine and 0.5 ml of 1,3-diamino-propane are stirred for 24 h at 90° and then diluted with 20 ml of ethyl acetate and extracted with 2×10 ml of sodium chloride solution. The organic phase is dried, concentrated and crystallised from methylene chloride/diethyl ether to give N-[3-{N-(3-amino-propyl)-aminocarbonyl}-phenyl]-4-[2-(3-hydroxy-propyl-amino)-4-pyridyl]-2-pyrimidineamine;

Workup

  1. extractionextracted with 2×10 ml of sodium chloride solution
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customcrystallised from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-e95dea12efcf46abb4f2455c2c2c6569
Source dataset
uspto-grants-1998_03
Patent number
US05728708

Linked notes

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