3,4-dihydro-2H-pyran → 2-Amino-4-(5,6-dihydro-4H-pyran-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

HRID 1356088Notes

Reaction equation

HRID 1356088 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.C([Sn](Cl)(CCCC)CCCC)CCC.[NH2:26][C:27]1[N:32]=[C:31](Br)[C:30]([C:34]#[N:35])=[C:29]([S:36][CH3:37])[N:28]=1>C1COCC1.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>[NH2:26][C:27]1[N:32]=[C:31]([C:6]2[O:1][CH2:2][CH2:3][CH2:4][CH:5]=2)[C:30]([C:34]#[N:35])=[C:29]([S:36][CH3:37])[N:28]=1

Participants

8

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 15096Tributyltin ChlorideHCID 187532302-Amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrileHCID 178418306HCID 178418306, compound

Product 1

HCID 185073182-Amino-4-(5,6-dihydro-4H-pyran-2-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

From 3,4-dihydro-2H-pyran, tert-butyllithium and tributyltin chloride in THF. Then treatment with 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile and bis(triphenylphosphine)palladium(II) chloride in dioxane. ES-MS m/e (%): 271 (M+Na+, 39), 249 (M+H+, 100).

Sources & evidence

ORD record
ord-7723afc591ce4d99b29b53b48d55fed9
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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