N,N-Dimethylethylenediamine → Ammonium Hydroxide

HRID 2243752Notes

Reaction equation

HRID 2243752 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:29]=[CH:30][C:31]=3[CH3:32])[C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37].[CH3:38][N:39]([CH2:41][CH2:42][NH2:43])[CH3:40]>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:43][CH2:42][CH2:41][N:39]([CH3:40])[CH3:38])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:29]=[CH:30][C:31]=3[CH3:32])[C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:37]

Participants

5

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 59208006HCID 59208006, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208127HCID 59208127, 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-diethyl-4-methylbenzamide (0.053 g, 0.1 mmol) was dissolved in THF (5 mL) and dimethylaminoethylamine (0.044 g, 0.5 mmol) was added. The reaction was stirred under argon overnight. 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 125-127° C. LC-MS m/z 538 (M+H)+, 1.57 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-4ee0d76e44e947faaa202d78f6b944ee
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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