N,N-Dimethylethylenediamine → HCID 58935450, compound

HRID 855506Notes

Reaction equation

HRID 855506 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[N:15]=[C:16]([Br:18])[S: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[N:15]=[C:16]([Br:18])[S: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 58935444HCID 58935444, compound

Product 1

HCID 58935450HCID 58935450, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-benzyl-2-bromo-5-(1-bromopropyl)[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one (1-2, 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 6-benzyl-2-bromo-5-(1-{[2-(dimethylamino)ethyl]-amino}propyl)[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one (1-3).

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-bfaf803aed7945429ff19b43a000952f
Source dataset
uspto-grants-2007_08
Patent number
US07262187B2

Reaction notes

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