3-(Dibutylamino)propylamine → Ammonium Hydroxide

HRID 2243761Notes

Reaction equation

HRID 2243761 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].[NH2:35][CH2:36][CH2:37][CH2:38][N:39]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40][CH2:41][CH2:42][CH3:43]>C1COCC1>[NH4+:9].[OH-:23].[CH2:40]([N:39]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:38][CH2:37][CH2:36][NH:35][C:16]1[N:17]=[C:18]([C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:13]2[CH2:12][NH:11][C:10](=[O:34])[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[C:14]=2[N:15]=1)[CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 2

HCID 16263-(Dibutylamino)propylamineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208049HCID 59208049, 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 (0.03 g, 0.062 mmol) was dissolved in THF (5 mL) and (3-aminopropyl)dibutylamine (0.058 g, 0.31 mmol) was added. The reaction was stirred under argon for 24 h. The solvents were pumped off in vacuo, and 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 112-115° C. LC-MS m/z 594.6 (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-9d5577181ec84d3d89aefb47eb8717ae
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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