Sodium Iodide → HCID 67063031, compound

HRID 599276Notes

Reaction equation

HRID 599276 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[C:5]#[N:6].Cl[CH2:14][C:15]1[C:16]([NH:23][CH:24]([CH3:26])[CH3:25])=[N:17][C:18]([S:21][CH3:22])=[N:19][CH:20]=1.[I-].[Na+].C(N(C(C)C)CC)(C)C>CC#N>[CH:24]([NH:23][C:16]1[C:15]([CH2:14][NH:1][C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=2)[C:5]#[N:6])=[CH:20][N:19]=[C:18]([S:21][CH3:22])[N:17]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 112289743-Amino-5-nitrobenzonitrileHCID 67063016HCID 67063016, compound

Product 1

HCID 67063031HCID 67063031, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 3-amino-5-nitrobenzonitrile (3.59 g, 22 mmol) in CH3CN (10 mL) was added dropwise to a mixture of 5-(chloromethyl)-N-isopropyl-2-(methylthio)pyrimidin-4-amine from Example A9 (5 g, 22 mmol), sodium iodide (0.33 g, 2.2 mmol), and diisopropylethylamine (2 mL, 12 mmol) in CH3CN (100 mL) at 0° C. The resultant reaction mixture was stirred at RT overnight. The solvent was evaporated and the residue was diluted with water, and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), concentrated and purified by silica gel chromatography to afford 3-((4-(isopropylamino)-2-(methylthio)pyrimidin-5-yl)methylamino)-5-nitrobenzonitrile (2.2 g, 28% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.87 (s, 1 H), 7.74 (s, 1 H), 7.56 (s, 1 H), 7.32 (s, 1H), 7.08 (m, 1 H), 6.63 (d, J=7.6 Hz, 1 H), 4.30 (m, 1 H), 4.15 (s, 2 H), 2.50 (s, 3 H), 1.17-1.15 (d, J=6.4 Hz, 6 H); MS (ESI) m/z: 359.2[M+H]+.

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f3ee316e380c46299359141beff24a26
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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