Tributyltin Chloride → 7-(1-Methyl-1-triethylsilanyloxyethyl)-3-tributylstannanylimidazo[1,2-alpha]pyrimidine

HRID 2184005Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([CH3:21])([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:27]([Sn:31](Cl)([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>O1CCCC1>[CH3:12][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([Sn:31]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:3][N:4]=[C:5]2[N:10]=1)([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of 3-bromo-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (440 mg, 1.20 mmol) in tetrahydrofuran (4 ml) was added isopropylmagnesium chloride (0.63 ml of a 2M solution in tetrahydrofuran, 1.26 mmol). After stirring at −78° C. for 5 min tributyltin chloride (0.36 ml, 1.32 mmol) was added, the reaction stirred for 10 min at −78° C., then allowed to warm to ambient temperature, to give a solution of 7-(1-methyl-1-triethylsilanyloxyethyl)-3-tributylstannanylimidazo[1,2-α]pyrimidine: m/z (ES+) 581 (M++H).

Workup

additionwas added
temperatureto warm to ambient temperature

Sources & evidence

ORD record: ord-fc8901b2079848de83ec99e196d3b273
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

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