Cesium carbonate → Tert-butyl (3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)carbamate

HRID 1846761Notes

Reaction equation

Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[OH:9][CH:10]1[CH2:13][CH:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[Cl:8][C:7]1[C:2]([O:9][CH:10]2[CH2:11][CH:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:13]2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2,3-dichloro-pyrazine (3.0 g, 20 mmol) and tert-butyl (3-hydroxycyclobutyl)carbamate (see PREPARATION 4B; 3.65 g, 20 mmol) in DMSO (50 mL) was added Cs2CO3 (13.2 g, 40 mmol), and then the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with water and filtered. The filtrate cake was washed with water, and dried to give tert-butyl (3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)carbamate (4.5 g, 15.2 mmol, 76%). ESI-MS (M+1): 300 calc. for C13H18ClN3O3 299.

Workup

filtrationfiltered
washThe filtrate cake was washed with water
customdried

Sources & evidence

ORD record: ord-c187325b03f340329a0111ef9590280b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952037B2

Reaction notes

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