4-Amino-1-methylpiperidine → Ammonium Hydroxide

HRID 2243763Notes

Reaction equation

HRID 2243763 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:26]=[CH:27][C:28]=3[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:34].[CH3:35][N:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]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]([NH:42][CH:39]3[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:34]

Participants

5

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208051HCID 59208051, 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,4-dimethylbenzamide, (0.02 g, 0.041 mmol) was dissolved in THF (5 mL) and 1-methyl-4-piperidinamine (0.024 g, 0.21 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, but the reaction had not gone to completion. The reaction was heated to 45° C. for 24 h and then cooled to room temperature. The solvents were pumped off in vacuo, and the residue was flash chromatographed on silica gel (10 g) eluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2:ethanol:NH4OH to give the title compound as a white amorphous solid. mp (dec) 205-209° C. LC-MS m/z 522 (M+H)+, 1.29 min (ret time).

Workup

  1. temperatureThe reaction was heated to 45° C. for 24 h
  2. temperaturecooled to room temperature
  3. customchromatographed on silica gel (10 g)
  4. washeluted with CH2Cl2 to 6:0.5:0.05, CH2Cl2

Sources & evidence

ORD record
ord-cd7e49df0c164c4a92336903bd28c63c
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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