Tributyl(4,5-dihydrofuran-2-yl)stannane → 2-Amino-4-(4,5-dihydro-furan-2-yl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile

HRID 1356122Notes

Reaction equation

[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]([C:9]#[N:10])=[C:6](Cl)[N:7]=1.C([Sn](CCCC)(CCCC)[C:17]1[O:18][CH2:19][CH2:20][CH:21]=1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]([C:9]#[N:10])=[C:6]([C:17]2[O:18][CH2:19][CH2:20][CH:21]=2)[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 200 mg (1.17 mmol) 2-amino-4-chloro-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile in 10 ml dioxane under argon at room temperature were added 463 mg (1.29 mmol) tributyl-(4,5-dihydro-furan-2-yl)-stannane and 82 mg (0.12 mmol) bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was heated at 100° C. for 16 h, then cooled to room temperature and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/1 then ethyl acetate then 5/95 methanol/ethyl acetate) afforded 65 mg (27%) 2-amino-4-(4,5-dihydro-furan-2-yl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile as a light yellow crystalline solid. ES-MS m/e (%): 205 (M+H+, 100).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c65ba075cf234634b3de867cb8fbe5ca
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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