Tributyltin Chloride → 2-Methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine

HRID 1812062Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.C([Mg]Cl)(C)C.Cl[Sn:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21]>C1COCC1>[CH3:10][C:4]1[N:5]=[C:6]([S:8][CH3:9])[CH:7]=[C:2]([Sn:17]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:18][CH2:19][CH2:20][CH3:21])[N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4-iodo-2-methyl-6-(methylthio)pyrimidine (2.35 g, 8.83 mmol) in THF (20 mL) was cooled to −78° C. and treated dropwise with isopropylmagnesium chloride (2 N solution in THF, 2 mL, 4.0 mmol, Aldrich). After 10 min, chlorotributylstannane (2.4 mL, 8.83 mmol, Aldrich) was added. The mixture was stirred at −78° C. for 1 h, then warmed to room temperature and stirred overnight. The mixture was concentrated in vacuo and purified by flash column chromatography with alumina, eluting with a gradient of 0-10% EtOAc in hexane, to give 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (2.5 g, 5.82 mmol, 65.9% yield) as colorless oil. This was used as such without further purification. m/z (ESI, +ve ion) 430 (M+H)+.

Workup

temperaturewarmed to room temperature
stirringstirred overnight
concentrationThe mixture was concentrated in vacuo
custompurified by flash column chromatography with alumina
washeluting with a gradient of 0-10% EtOAc in hexane

Sources & evidence

ORD record: ord-ea806611758f493187bf3bfe16a50d0b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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