1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178510878, compound

HRID 1692948Notes

Reaction equation

[Si]([O:18][CH:19]1[CH2:22][C:21](=[CH:23][C:24]#[N:25])[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH:26]1[CH:30]=[C:29]([C:31]2[C:32]3[CH:39]=[CH:38][N:37](COCC[Si](C)(C)C)[C:33]=3[N:34]=[CH:35][N:36]=2)[CH:28]=[N:27]1.N12CCCN=C1CCCCC2>C(#N)C>[OH:18][CH:19]1[CH2:20][C:21]([CH2:23][C:24]#[N:25])([N:26]2[CH:30]=[C:29]([C:31]3[N:36]=[CH:35][NH:34][C:33]4=[N:37][CH:38]=[CH:39][C:32]=34)[CH:28]=[N:27]2)[CH2:22]1

Participants

Conditions

Temperature: 50 °C

Procedure

(3-[tert-Butyl(diphenyl)silyl]oxycyclobutylidene)acetonitrile (0.15 g, 0.00043 mol) was combined with 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (0.14 g, 0.00043 mol) in acetonitrile (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.064 mL, 0.00043 mol) was added under nitrogen. The mixture was heated to 50° C. over night. LCMS showed a peak with m/z of 425.4, indicating a de-silyl reaction occurred simultaneously during the Micheal addition. The reaction was concentrated and purified on combiflash (silica gel, 0-100% EtOAc/Hex) to yield the desired produt. LCMS (M+H) 425.4.

Workup

additionwas added under nitrogen
customa de-silyl reaction
additionoccurred simultaneously during the Micheal addition
concentrationThe reaction was concentrated
custompurified on combiflash (silica gel, 0-100% EtOAc/Hex)
customto yield the desired produt

Sources & evidence

ORD record: ord-4e1f08f4e2264e0dbbedf24f429348ed
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158616B2

Reaction notes

Loading…