Pyrimidine → 4-(Tributylstannyl)pyrimidine

HRID 1359283Notes

Reaction equation

HRID 1359283 reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>O.O1CCCC1.CCCCCC>[N:16]1[CH:21]=[CH:20][C:19]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:18][CH:17]=1

Participants

8

Reactant 4

HCID 9260PyrimidineHCID 130352,2,6,6-TetramethylpiperidineHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 178300604-(Tributylstannyl)pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

5.8 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added dropwise into a solution of 20 ml of tetrahydrofuran containing 2.5 ml of 2,2,6,6-tetramethylpiperidine. After stirring at 0° C. for 30 minutes, a mixture of 0.98 ml of pyrimidine, 4.6 ml of tri-n-butyltin chloride and 20 ml of tetrahydrofuran was slowly added dropwise thereinto. After stirring at −78° C. for 4 hours, water was added to the reaction solution and then extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to silica gel column chromatography to elute with hexane/ethyl acetate (10:1), to give 474 mg of the target compound.

Workup

  1. additionwas slowly added dropwise
  2. stirringAfter stirring at −78° C. for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customthe solvent was removed
  6. washto elute with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-8546d8822e6c42818a7233f527c31070
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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