Tributyltin Chloride → HCID 59486262, compound

HRID 912553Notes

Reaction equation

HRID 912553 reaction equation
C([Mg]Cl)(C)C.I[C:7]1[CH:12]=[C:11]([S:13][CH3:14])[N:10]=[CH:9][N:8]=1.[Sn:15](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1>[CH3:14][S:13][C:11]1[CH:12]=[C:7]([Sn:15]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:16][CH2:17][CH2:18][CH3:19])[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 59486258HCID 59486258, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59486262HCID 59486262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of iPrMgCl (2M in THF solution, 5 mL, 10 mmol) is added slowly to a solution of 4-iodo-6-methylsulfanyl-pyrimidine 35 (2.53 g, 10 mol) in THF (50 mL) at −78° C. After 10 minutes, Bu3SnCl (2.75 mL, 10 mmol) is added. After reaction overnight, the reaction mixture is concentrated. The crude product is purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 0% to 10% to afford 4-methylsulfanyl-6-tributylstannanyl-pyrimidine (36).

Workup

  1. customAfter reaction overnight
  2. concentrationthe reaction mixture is concentrated
  3. customThe crude product is purified by silica gel flash chromatography
  4. washeluting with ethyl acetate in hexanes from 0% to 10%

Sources & evidence

ORD record
ord-22e815d3b86a49c6ac908cb3f83545aa
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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