Tributyltin Chloride → HCID 59486262, compound

HRID 710569Notes

Reaction equation

HRID 710569 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.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1>[CH3:14][S:13][C:11]1[CH:12]=[C:7]([Sn:19]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][CH2:17][CH3:18])[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 isopropylmagnesium chloride (2M in THF solution, 5 mL, 10 mmol) was added slowly to a solution of 4-iodo-6-methylsulfanyl-pyrimidine (2.53 g, 10 mol) in THF (50 mL) at −78° C. After 10 min, tri-n-butyltin chloride (2.75 mL, 10 mmol) was added, and the mixture was stirred and allowed to warm to rt overnight. The crude product was purified by silica gel flash chromatography (0 to 10% ethyl acetate in hexanes eluant) to afford the title compound.

Workup

  1. customThe crude product was purified by silica gel flash chromatography (0 to 10% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-6fb221c139c04422b523811534c71e0d
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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