N,N-Dimethylethylenediamine → HCID 178457400, compound

HRID 855501Notes

Reaction equation

HRID 855501 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Br:18])=[N:16][NH: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[C:15]([Br:18])=[N:16][NH: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 178438276HCID 178438276, compound

Product 1

HCID 178457400HCID 178457400, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-benzyl-3-bromo-6-(1-bromopropyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-3, 5.0 g, 11.7 mmol, 1 equiv) and N,N-dimethylethylenediamine (2.6 g, 29.3 mmol, 2.5 equiv) in ethanol (25 mL) was heated at reflux for 18 h. The reaction was concentrated, and the residue was purified by flash chromatography. Elution with CH2Cl2 to 25% NH3-EtOH/(CH2Cl2 gave 5-benzyl-3-bromo-6-(1-{[2-(dimethylamino)ethyl]amino}propyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-4) as a light green foam. 1H NMR (500 MHz, CDCl3) δ 11.1 (bs, 1H), 7.33 (m, 2H), 7.29 (m, 1H), 7.15 (d, J=7 Hz), 5.97 (d, J=16 Hz), 4.71 (d, J=16 Hz), 3.58 (m, 1H), 2.52 (m, 1H), 2.30 (m, 2H), 2.24 (s, 6H), 1.94 (m, 1H), 1.52 (m, 1H), 1.31 (m, 1H), 0.84 (t, J=7 Hz, 3H).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationThe reaction was concentrated
  3. customthe residue was purified by flash chromatography
  4. washElution with CH2Cl2 to 25% NH3-EtOH/(CH2Cl2

Sources & evidence

ORD record
ord-6f1e657656d442c79d84925de18646f1
Source dataset
uspto-grants-2007_08
Patent number
US07262186B2

Reaction notes

Loading…