N-Isopropylpropane-1,3-diamine → Ammonium Hydroxide

HRID 2243758Notes

Reaction equation

HRID 2243758 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][CH:40]([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][CH:40]([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 76888N-Isopropylpropane-1,3-diamineHCID 11950623HCID 11950623, compound

Product 2

HCID 14923Ammonium HydroxideHCID 59208067HCID 59208067, 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-methylethyl)amine (0.045 g, 0.37 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 (dec) 153-157° C. LC-MS m/z 524.6 (M+H)+, 1.31 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-f4658cf4a46d4ccbb80a9919580965e5
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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