N,N-Dimethylethylenediamine → HCID 58909205, compound

HRID 1295614Notes

Reaction equation

HRID 1295614 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[C:16]([Br:18])[O:17][C:11]=2[N:10]=[C:9]1[CH:19](Br)[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27]>C(O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[C:16]([Br:18])[O:17][C:11]=2[N:10]=[C:9]1[CH:19]([NH:27][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 58909206HCID 58909206, compound

Product 1

HCID 58909205HCID 58909205, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-benzyl-6-bromo-2-(1-bromopropyl)furo[2,3-d]pyrimidin-4(3H)-one (1-4, 1 equiv) and N,N-dimethylethylenediamine (3 equiv) in ethanol is heated at reflux for 18 h. The reaction mixture is concentrated, and the residue is partitioned between EtOAc and brine. The organic layer is dried (MgSO4) and concentrated to provide 3-benzyl-6-bromo-2-(1-{[2-(dimethylamino)-ethyl]amino}propyl)furo[2,3-d]pyrimidin-4(3H)-one (1-5)

Workup

  1. temperatureat reflux for 18 h
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue is partitioned between EtOAc and brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d0e42c5e9b2044b0840ec97c4187d3e5
Source dataset
uspto-grants-2007_07
Patent number
US07244723B2

Reaction notes

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