N,N'-Dimethylethylenediamine → HCID 121249607, compound

HRID 632841Notes

Reaction equation

HRID 632841 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[C:13](=[O:19])[NH:14][CH:15]=[CH:16][C:17]=3[CH3:18])[CH2:9][CH2:8][C:6]=2[N:7]=1.I[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=1.CNCCNC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN1CCCC1=O.[Cu](I)I>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[C:13](=[O:19])[N:14]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 6379581-tert-butyl-3-iodobenzeneHCID 1212495913-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one

Product 1

HCID 121249607HCID 121249607, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A degassed solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one (0.025 g, 0.097 mmol), 1-iodo-3-tertbutyl benzene (0.20 g, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (0.005 g, 0.049 mmol), Copper Iodide (0.004 g, 0.020 mmol), and Potassium Phosphate (0.041 g, 0.194 mmol) in 0.5 mL of N-methylpyrrolidone was heated to 70° C. After allowing the reaction to stir overnight (17 h) at 70° C., the reaction was complete and allowed to cool to room temperature. The reaction was extracted with 3×'s with EtOAc (˜5 mL) and 2×'s with NaHCO3 (˜10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and the concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using an 0-100% EtOAc gradient/100-0% Hexane gradient mixture. After concentrating the appropriate fractions, the pure product was collected as an off white solid (5 mg, 19%). 1H NMR (DMSO) δ: 7.94 (s, 1H), 7.46-7.55 (m, 2H), 7.47 (m, 1H), 7.28-7.36 (m, 2H), 6.32 (s, 2H), 6.21 (m, 1H), 3.96 (br. S, H), 3.29 (s, 2H), 2.66(t, j=5.3 Hz, 2H), 2.25 (s, 3H), 2.09 (s, 9H).

Workup

  1. customthe reaction
  2. temperatureto cool to room temperature
  3. extractionThe reaction was extracted with 3×'
  4. dry with materialdried over anhydrous Na2SO4 (s)
  5. filtrationfiltered
  6. concentrationthe concentrated in vacuo
  7. customThe crude mixture was then purified
  8. concentrationAfter concentrating the appropriate fractions
  9. customthe pure product was collected as an off white solid (5 mg, 19%)

Sources & evidence

ORD record
ord-5182d9dd4bf44c2e93ddd001a54c46c0
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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