Tributyltin Chloride → 7-([1,2,4]Triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-alpha]pyrimidine

HRID 1796103Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)=[N:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].[SnH4]>O1CCCC1>[N:12]1([CH2:11][C:9]2[CH:8]=[CH:7][N:6]3[C:2]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:3][N:4]=[C:5]3[N:10]=2)[CH:16]=[N:15][CH:14]=[N:13]1

Participants

Conditions

Temperature: -45 °C

Procedure

To a cooled (−78° C.) solution of 3-bromo-7-([1,2,4]triazol-1-ylmethyl)-imidazo[1,2-α]pyrimidine (0.42 g, 1.50 mmol) in tetrahydrofuran (15 ml) was added isopropylmagnesium chloride (0.82 ml of a 2M solution in tetrahydrofuran, 2.37 mmol). Mixture was allowed to warm to −45° C. and stirring at this temperature was continued for 0.5 h. Mixture was recooled to −78° C., tributyltin chloride (0.47 ml, 1.72 mmol) added in a dropwise fashion, stirred for 10 min at −78° C. and then allowed to warm to ambient temperature. This process of Grignard formation with subsequent transmetallation to the stannane intermediate was repeated to encourage completion of the reaction giving 7-([1,2,4]triazol-1-ylmethyl)-3-tributylstannylimidazo[1,2-α]pyrimidine as a solution in tetrahydrofuran (ca. 0.1M); m/z (ES+) 487, 489, 490 (M++H).

Workup

customwas recooled to −78° C.
stirringstirred for 10 min at −78° C.
temperatureto warm to ambient temperature

Sources & evidence

ORD record: ord-28a7eb1af9954ef5a671287ccf7f61de
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030128B2

Reaction notes

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