1-Methylpiperazine → Ammonium Hydroxide

HRID 2243747Notes

Reaction equation

HRID 2243747 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].[CH3:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>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]([N:45]3[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]3)[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 531671-MethylpiperazineHCID 11950098HCID 11950098, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208004HCID 59208004, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 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 (0.056 g, 0.1 mmol) was dissolved in THF (5 mL) and 1-methylpiperazine (0.0303 g, 0.3 mmol) was added. The reaction was stirred for 72 h. The solvents were pumped off in vacuo, and the residue taken up in EtOAc and washed with 1 N NaOH, brine, dried over anhydrous Na2SO4 filtered and evaporated. The residue was flash chromatographed on silica gel (20 g) eluted with 6:0.1:0.01 to 6:0.3:0.03, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp 164-168° C. LC-MS m/z 584 (M+H)+, 1.85 min (ret time).

Workup

  1. washwashed with 1 N NaOH, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customchromatographed on silica gel (20 g)
  6. washeluted with 6:0.1:0.01 to 6:0.3:0.03, CH2Cl2

Sources & evidence

ORD record
ord-965461123a394f14b42f7246dba2546f
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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