Sodium Iodide → HCID 59420848, compound

HRID 474017Notes

Reaction equation

HRID 474017 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[C:4](Cl)[N:3]=1.[I-].[Na+].[NH2:17][C:18]1[CH:22]=[C:21]([CH3:23])[NH:20][N:19]=1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH3:23][C:21]1[NH:20][N:19]=[C:18]([NH:17][C:4]2[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=2)[CH:22]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 59420814HCID 59420814, compound

Product 1

HCID 59420848HCID 59420848, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-(2,6-dichloropyrimidin-4-yl)acetate (1.0 g, 4.25 mmol), sodium iodide (0.637 g, 4.25 mmol), 3-amino-5-methylpyrazole (0.413 g, 4.25 mmol), and N,N-diisopropylethylamine (0.96 ml, 5.53 mmol) was heated at 90° C. until reaction was complete (˜3 h). Reaction mixture was then cooled to room temperature, diluted with ethyl acetate (100 ml), washed with sat. sodium hydrogen carbonate solution (1×30 ml), water (3×30 ml), brine (30 ml), dried (MgSO4), filtered and evaporated in vacuo to leave an orange oil. Crude product was purified by flash chromatography (SiO2, 60-100% EtOAc/Petrol) to give title compound as a red sticky oil (0.520 g, 41%). 1H NMR (CDCl3) 1.29 (3H, t), 2.41 (3H, s), 3.52 (2H, s), 4.23 (2H, q), 5.20-4.60 (2H, very broad signal); ES+296.

Workup

  1. custom(˜3 h)
  2. customReaction mixture
  3. washwashed with sat. sodium hydrogen carbonate solution (1×30 ml), water (3×30 ml), brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto leave an orange oil
  8. customCrude product was purified by flash chromatography (SiO2, 60-100% EtOAc/Petrol)

Sources & evidence

ORD record
ord-477c6576f9064d4fbdd71dd036d1a2b3
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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