1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86634347, compound

HRID 1692940Notes

Reaction equation

[C:1]1([CH2:11][C:12]#[N:13])([CH2:8][C:9]#[N:10])[CH2:4][C:3](=[CH:5][C:6]#[N:7])[CH2:2]1.[NH:14]1[CH:18]=[C:17]([C:19]2[C:20]3[CH:27]=[CH:26][N:25]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH:16]=[N:15]1.N12CCCN=C1CCCCC2>C(#N)C>[CH3:33][Si:32]([CH3:35])([CH3:34])[CH2:31][CH2:30][O:29][CH2:28][N:25]1[C:21]2[N:22]=[CH:23][N:24]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([C:3]4([CH2:5][C:6]#[N:7])[CH2:2][C:1]([CH2:8][C:9]#[N:10])([CH2:11][C:12]#[N:13])[CH2:4]4)[CH:18]=3)[C:20]=2[CH:27]=[CH:26]1

Participants

Conditions

Temperature: 50 °C

Procedure

The crude 2,2′,2″-cyclobutane-1,1-diyl-3-ylidenetriacetonitrile (1 g, 0.006 mol) was combined with 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (0.2 g, 0.0006 mol) in acetonitrile (10 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.1 mL, 0.001 mol) was added under nitrogen. The mixture was heated at 50° C. over night. The reaction was concentrated and purified with Combiflash (silica gel, 0-100% EtOAc/Hex) to give the desired product as light brown oil. LCMS calculated for C25H31N8OSi(M+H)+: 487.2; Found: 487.4.

Workup

additionwas added under nitrogen
concentrationThe reaction was concentrated
custompurified with Combiflash (silica gel, 0-100% EtOAc/Hex)

Sources & evidence

ORD record: ord-af1b52319fa8490e829aadeaa52f47dc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158616B2

Reaction notes

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