Hydrochloric Acid → 6-(2-chloro-5-nitrophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1517244Notes

Reaction equation

HRID 1517244 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:24](=[O:25])[N:23]([O:26][CH3:27])[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[CH:18][C:13]=2[CH:12]=1.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32].Cl>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:24](=[O:25])[N:23]([O:26][CH3:27])[C:14]2[N:15]=[C:16]([NH:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])[N:17]=[CH:18][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66053N,N-DimethylethylenediamineHCID 674425136-(2-Chloro-5-nitrophenyl)-8-methoxy-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 674430196-(2-chloro-5-nitrophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(2-Chloro-5-nitrophenyl)-8-methoxy-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (4.87 mmol), N,N-dimethylethane-1,2-diamine (11.3 mmol), and conc. aq. hydrochloric acid (2.0 mL) were placed in a microwave vessel and dissolved in 2-propanol (18 mL). The mixture was heated with microwave irradiation in a sealed vessel at 100° C. for 15 min. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc. The organic layer was washed with water and aqueous buffer (aq. KH2PO4 and NaOH. pH 7.0). The aqueous layer was backextracted with EtOAc (4×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give solid 6-(2-chloro-5-nitrophenyl)-2-(2-(dimethylamino)ethylamino)-8-methoxypyrido[2,3-d]pyrimidin-7(8H)-one that was used without furoom temperatureher purification (53%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and aqueous buffer (aq. KH2PO4 and NaOH. pH 7.0)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-791eea3215af437892ad203c815b383f
Source dataset
uspto-grants-2012_07
Patent number
US08232283B2

Reaction notes

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