N,N-Diethyl-1,3-propanediamine → Ammonium Hydroxide

HRID 2243762Notes

Reaction equation

HRID 2243762 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]([CH2:42][CH3:43])[CH2:40][CH3:41]>C1COCC1>[NH4+:9].[OH-:23].[CH2:40]([N:39]([CH2:42][CH3:43])[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)[CH3:41]

Participants

5

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59207988HCID 59207988, 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)diethylamine (0.041 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 133-136° C. LC-MS m/z 538 (M+H)+, 1.34 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-287d0e44ce804b5e9e5cf662430a2094
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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