1,3-Propanediamine, N1,N1,N3-trimethyl- → Ammonium Hydroxide

HRID 2243764Notes

Reaction equation

HRID 2243764 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]([CH3:42])[CH2:37][CH2:38][CH2:39][NH:40][CH3:41]>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]([CH2:39][CH2:38][CH2:37][N:36]([CH3:42])[CH3:35])[CH3:41])[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 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208141HCID 59208141, 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 [3-(dimethylamino)propyl]methylamine (0.024 g, 0.205 mmol) was added. The reaction mixture was stirred at room temperature for 6 days, but the reaction had not gone to completion. The reaction was heated to 45° C. overnight 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 163-165° C. LC-MS m/z 524.6 (M+H)+, 1.47 min (ret time).

Workup

  1. temperatureThe reaction was heated to 45° C. overnight
  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-4e7cad1f87794a01af99b569b2cafc6b
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…