N,N-Dimethylethylenediamine → HCID 59716440, compound

HRID 2224100Notes

Reaction equation

HRID 2224100 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Br:19])=[C:16]([Br:18])[S:17][C:11]=2[N:10]=[C:9]1[CH:20](Br)[CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][NH2:28]>C(O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Br:19])=[C:16]([Br:18])[S:17][C:11]=2[N:10]=[C:9]1[CH:20]([NH:28][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])[CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 59716452HCID 59716452, compound

Product 1

HCID 59716440HCID 59716440, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-benzyl-5,6-dibromo-2-(1-bromopropyl)thieno[2,3-d]pyrimidin-4(3H)-one (2-5, 35 mg, 0.066 mmol, 1 equiv) and N,N-dimethylethylenediamine (17 mg, 0.198 mmol, 3 equiv) in ethanol (5 mL) was heated at reflux for 18 h. The reaction was concentrated, and the residue was partitioned between EtOAc and brine. The organic layer was dried (MgSO4) and concentrated to provide 3-benzyl-5,6-dibromo-2-{(1-([2-(dimethylamino)ethyl]amino}propyl)thieno-[2,3-d]pyrimidin-4(3H)-one (2-7) as a yellow gum. MS(M+1)=526.8.

Workup

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

Sources & evidence

ORD record
ord-5e3306569eb84227946821efbf3c1163
Source dataset
uspto-grants-2008_05
Patent number
US07378411B2

Reaction notes

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