Tributyl(2,3-dihydrofuran-5-yl)stannane → 2-Amino-4-(4,5-dihydro-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356087Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Br)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[O:19][CH2:20][CH2:21][CH:22]=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[N:7]=[C:6]([C:18]2[O:19][CH2:20][CH2:21][CH:22]=2)[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 700 mg (2.86 mmol) 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile in 25 ml dry dioxane under argon at room temperature were added 1.13 g (3.14 mmol) tributyl-(4,5-dihydro-furan-2-yl)-stannane and 281 mg (0.40 mmol) bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/1) afforded 325 mg (49%) 2-amino-4-(4,5-dihydro-furan-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile as a yellow crystalline solid. ES-MS m/e (%): 257 (M+Na+, 47), 235 (M+H+, 100).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-61088bec13a24ffc975fe7cb8f17ddd8
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586441B2

Reaction notes

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