Tributyltin Chloride → 3-Tributylstannylimidazo[1,2-alpha]pyrimidine

HRID 2183957Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1)[CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of 3-bromoimidazo[1,2-α]pyrimidine (500 mg, 2.5 mmol) in tetrahydrofuran (20 ml) was added isopropylmagnesium chloride (1.39 ml of a 2.0M solution in tetrahydrofuran, 2.78 mmol). After stirring for 5 min tri-n-butyltin chloride (0.8 ml, 2.90 mmol) was added and the reaction stirred for 10 min at −78° C. then allowed to warm to ambient temperature to give a solution of 3-tributylstannylimidazo[1,2-α]pyrimidine in tetrahydrofuran: m/z (ES+) 407, 409, 411 (M++H).

Workup

additionwas added
temperatureto warm to ambient temperature

Sources & evidence

ORD record: ord-a7fe805bfc9c47fa9a6c5807e96c7788
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

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