Ethyl Acetate → HCID 58382377, compound

HRID 1628044Notes

Reaction equation

[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:16]4=[N:17][CH:18]=[C:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[N:20]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:45][C:46]([CH3:48])=[CH2:47].CCOC(C)=O>CN(C=O)C.O>[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:16]4=[N:17][CH:18]=[C:19]([N:21]([CH2:47][C:46]([CH3:48])=[CH2:45])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[N:20]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1

Participants

Conditions

Temperature: 65 °C

Procedure

tert-Butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.50 g, 0.95 mmol) and Cs2CO3 (1.55 g, 4.75 mmol) were combined in DMF (19 mL). 3-Bromo-2-methylpropene (0.191 mL, 1.90 mmol) was added and the mixture was heated at about 65° C. for about 3 h. EtOAc (50 mL) and water (50 mL) were added and the layers separated. The organic layer was washed with 5% aqueous LiCl (3×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl(2-methylallyl)carbamate (0.584 g, 106%): LC/MS (Table 2, Method h) Rt=2.43 min.; MS m/z: 581 (M+H)+.

Workup

customthe layers separated
washThe organic layer was washed with 5% aqueous LiCl (3×15 mL) and brine (15 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4e77d918e4b541f69e4ef10f348ab1b0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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