1,8-Diazabicyclo(5.4.0)undec-7-ene → diisopropyl 3-(cyanomethyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutane-1,1-dicarboxylate

HRID 1692934Notes

Reaction equation

[C:1]([CH:3]=[C:4]1[CH2:7][C:6]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH2:5]1)#[N:2].[NH:20]1[CH:24]=[C:23]([C:25]2[C:26]3[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:27]=3[N:28]=[CH:29][N:30]=2)[CH:22]=[N:21]1.N12CCCN=C1CCCCC2>C(#N)C>[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[C:26]4[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:27]=4[N:28]=[CH:29][N:30]=3)[CH:22]=[N:21]2)[CH2:5][C:6]([C:8]([O:10][CH:11]([CH3:12])[CH3:13])=[O:9])([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH2:7]1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Diisopropyl 3-(cyanomethylene)cyclobutane-1,1-dicarboxylate (2.65 g, 0.00999 mol) was combined with 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (1 g, 0.003 mol) in acetonitrile (10 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.5 mL, 0.003 mol) was added under N2. The mixture was heated at 50° C. overnight. The reaction was concentrated and purified with Combiflash (silica gel, 0-50% EtOAc/Hex) to give the desired product (0.3 g) as colorless oil. LCMS calculated for C29H41N6O5Si(M+H): 581.3; Found: 581.4.

Workup

additionwas added under N2
concentrationThe reaction was concentrated
custompurified with Combiflash (silica gel, 0-50% EtOAc/Hex)

Sources & evidence

ORD record: ord-289d54c96d494e13bac3deae6757d16d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158616B2

Reaction notes

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