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

HRID 2243664Notes

Reaction equation

HRID 2243664 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:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40].[CH3:41][N:42]([CH3:48])[CH2:43][CH2:44][CH2:45][NH:46][CH3:47]>C1COCC1.CCOC(C)=O>[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:46]([CH2:45][CH2:44][CH2:43][N:42]([CH3:48])[CH3:41])[CH3:47])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40]

Participants

6

Reactant 2

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-2×HCID 11950098HCID 11950098, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11952231HCID 11952231, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide, (0.050 g, 0.089 mmol) was dissolved in THF (5 mL) and N,N,N′-trimethyl-1,3-propanediamine (0.054 g, 0.44 mmol) was added. The mixture was stirred under argon at room temperature for 3 h. The reaction was not complete, so additional N,N,N′-trimethyl-1,3-propanediamine (0.108 g, 0.88 mmol) was added and the mixture stirred at room temperature for an additional 17 h, followed by heating to 400 C for 1 h. The solvents were pumped off in vacuo. The residue was taken up in EtOAc washed with 1M NaOH (2×), brine (1×), dried over anhydrous Na2SO4, filtered and evaporated. The residue was flash chromatographed on silica gel (20 g) eluted with 6:1:0.05, CH2Cl2:isopropanol:NH4OH to give the title compound as a white amorphous solid. mp 124-127° C.; LC-MS m/z 600 (M+H)+, 1.84 min (ret. time).

Workup

  1. stirringthe mixture stirred at room temperature for an additional 17 h
  2. temperatureby heating to 400 C for 1 h
  3. washwashed with 1M NaOH (2×), brine (1×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed on silica gel (20 g)
  8. washeluted with 6:1:0.05, CH2Cl2

Sources & evidence

ORD record
ord-bd62cfac6bf543ce9c1e9c590d970e68
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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