N-(1,1-Dimethylethyl)-1,3-propanediamine → Ammonium Hydroxide

HRID 2243760Notes

Reaction equation

HRID 2243760 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][NH:39][C:40]([CH3:43])([CH3:42])[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]([NH:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]([CH3:43])([CH3:42])[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 40274N-(1,1-Dimethylethyl)-1,3-propanediamineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59207983HCID 59207983, 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 (0.036 g, 0.074 mmol) was dissolved in THF (5 mL) and (3-aminopropyl)(1,1-dimethylethyl)amine (0.045 g, 0.37 mmol) was added. The reaction was stirred under argon for 2 days. 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 (dec)166-170° C. LC-MS m/z 538 (M+H)+, 1.38 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-ea3837933fc44d75b1b967ad6639d2e7
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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