Tributyltin Chloride → 4-Chloro-6-(tributylstannyl)thieno[3,2-d]pyrimidine

HRID 1818947Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Li+].CC([N-]C(C)C)C.[Sn:19](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23].[NH4+].[Cl-]>C1COCC1.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>[Cl:1][C:2]1[C:3]2[S:10][C:9]([Sn:19]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a flame dried flask was placed a suspension of compound 6.2 (5.92 mmol) in THF (50 mL). The reaction was cooled to −78° C. and a solution of LDA (3.25 mL of a 2.0 M solution in heptane/THF/ethyl benzene) was slowly added. After stirring for 30 minutes, a −78° C., a solution of (n-Bu)3SnCl (1.9 mL) in THF (50 mL) was added via cannula over a 20 minute period at −78° C. and stirred for 2 hours. The reaction was warmed to room temperature, hydrolyzed with saturated NH4Cl, extracted with EtOAc, dried and concentrated. The crude product was purified by flash column chromatography on silica gel (1:1 hexanes/dichloromethane then 10% EtOAc/dichloromethane) to provide 4-chloro-6-tributylstannanyl-thieno[3,2-d]pyrimidine (compound 52.1) in 92% yield.

Workup

customTo a flame dried flask
stirringstirred for 2 hours
extractionextracted with EtOAc
customdried
concentrationconcentrated
customThe crude product was purified by flash column chromatography on silica gel (1:1 hexanes/dichloromethane

Sources & evidence

ORD record: ord-3d6df94ef5284a28afd335c3b45a8423
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601725B2

Reaction notes

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