N-Isopropylethylenediamine → Ammonium Hydroxide

HRID 2243667Notes

Reaction equation

HRID 2243667 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40].[CH:41]([NH:44][CH2:45][CH2:46][NH2:47])([CH3:43])[CH3:42]>C1COCC1.CCOC(C)=O>[NH4+:9].[OH-:23].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:47][CH2:46][CH2:45][NH:44][CH:41]([CH3:43])[CH3:42])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40]

Participants

6

Reactant 2

HCID 88098N-IsopropylethylenediamineHCID 11950098HCID 11950098, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952410HCID 11952410, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide, (0.060 g, 0.106 mmol) was dissolved in THF (5 mL) and N-isopropylethylenediamine (0.1 g, 0.98 mmol) was added. The mixture was stirred under argon at room temperature for 3 h. The solvents were pumped off in vacuo. The residue was taken up in EtOAc washed with 1M NaOH (1×), brine (1×), dried over anhydrous Na2SO4, filtered and evaporated The residue was flash chromatographed on silica gel (10 g) eluted with 6:0.5:0.05, CH2Cl2:ethanol:NH4OH to give the title compound as a off-white amorphous solid. mp 133-137° C.; LC-MS m/z 586 (M+H)+, 1.5 min (ret. time).

Workup

  1. washwashed with 1M NaOH (1×), brine (1×)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated The residue
  5. customchromatographed on silica gel (10 g)
  6. washeluted with 6:0.5:0.05, CH2Cl2

Sources & evidence

ORD record
ord-bd442db9649a499497dfab4b1afaf1c4
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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