Sodium Iodide → HCID 66955897, compound

HRID 1399624Notes

Reaction equation

HRID 1399624 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+].[NH:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][CH2:36]1>CN1CCCC1=O.C(#N)C>[N:35]1([C:2]2[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:3]=2)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10328IndolineHCID 81531DiisopropylethylamineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955897HCID 66955897, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.104 g; 0.312 mmol), N,N-diisopropylethylamine (0.122 mL; 0.781 mmol), sodium iodide (0.047 mg; 0.312 mmol) and indoline (0.074 mL; 0.625 mmol) in a mixture of 1-methylpyrrolidin-2-one (0.5 mL) and acetonitrile (0.5 mL) was irradiated in a microwave oven at 160° C. for 30 min. The solution was partitioned between ethyl acetate and water and the organic layer was washed with a saturated solution of sodium thiosulphate, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica using a gradient of ethyl acetate (2-20%) in heptane furnished 0.040 g (31%) of the title compound as a yellow oil.

Workup

  1. customwas irradiated in a microwave oven at 160° C. for 30 min
  2. customThe solution was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with a saturated solution of sodium thiosulphate
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash-chromatography on silica using a gradient of ethyl acetate (2-20%) in heptane

Sources & evidence

ORD record
ord-9192897184f742cbbd06db0da888bbf0
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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