Sodium Iodide → HCID 70896639, compound

HRID 1619284Notes

Reaction equation

HRID 1619284 reaction equation
[C:1]([NH:5][C:6]([C:8]1[N:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:15].[Na+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[C:1]([NH:5][C:6]([C:8]1[N:13]=[CH:12][C:11]([I:15])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 674440355-bromo-N-tert-butylpyrimidine-2-carboxamide

Product 1

HCID 70896639HCID 70896639, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-pyrimidine-2-carboxylic acid tert-butylamide (Example 9, step 1) (950 mg, 3.68 mmol) was dissolved in dioxane (10 ml). Sodium iodide (2.2 g, 14.7 mmol, 4 equiv.), copper(I)iodide (66 mg, 0.74 mmol, 0.2 equiv.) and trans-N,N′-dimethylcyclohexane-1,2-diamine (CAS 67579-81-1) (105 mg, 0.74 mmol, 0.2 equiv.) were added and the mixture was stirred for 16 hours at 100° C. The reaction mixture was extracted with saturated NaHCO3 solution and two times with ethyl acetate. The organic layers were extracted with brine, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography with a 20 g silica gel column and eluting with heptane:ethyl acetate 100:0→0:100. The desired 5-iodo-pyrimidine-2-carboxylic acid tert-butylamide (870 mg, 78% yield) was obtained as a yellow solid, MS: m/e=306.0 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with saturated NaHCO3 solution and two times with ethyl acetate
  2. extractionThe organic layers were extracted with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography with a 20 g silica gel column
  6. washeluting with heptane:ethyl acetate 100:0→0:100

Sources & evidence

ORD record
ord-d35aab6d2a7144bb8cee04799170aa22
Source dataset
uspto-grants-2014_07
Patent number
US08772300B2

Reaction notes

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