1-Methylpiperazine → Ammonium Hydroxide

HRID 2243749Notes

Reaction equation

HRID 2243749 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:27]=[CH:28][C:29]=3[CH3:30])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:35].[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>C1COCC1>[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:40]3[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:35]

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 11950625HCID 11950625, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208129HCID 59208129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N,N,4-trimethylbenzamide (0.050 g, 0.1 mmol) was dissolved in THF (5 mL) and 1-methylpiperazine (0.050 g, 0.5 mmol) was added. The reaction was stirred under argon overnight. The solvents were pumped off in vacuo. The residue was flash chromatographed on silica gel (15 g) eluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp 159-162° C. LC-MS m/z 522 (M+H)+, 1.59 min (ret time).

Workup

  1. customchromatographed on silica gel (15 g)
  2. washeluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2

Sources & evidence

ORD record
ord-0af9afc8a8764f4da721a845ecbd198e
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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