tert-Butyl N-(2-bromoethyl)carbamate → HCID 58507731, compound

HRID 1408464Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:18]3[S:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.[C:35]([NH:42][CH2:43][CH2:44]Br)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C1COCC1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:18]3[S:23][C:22]([CH2:44][CH2:43][NH:42][C:35](=[O:36])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:21][C:19]=3[N:20]=2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

4-(2-(3-(tert-butyldimethylsilyloxy)phenyl)thieno[3,2-d]pyrimidin-4-yl)morpholine (166 mg, 388 μmol, 1.0 eq.) was solved with dry THF (3 ml) under room temperature and added to a round-two-neck flask that was heated under vacuum and flushed with nitrogen. The solution was then cooled to −78° C. and n-BuLi (315 μl, 1.6 M solution in hexanes, 1.3 eq.) was added dropwise. After stirring for 20 min., 2-(boc-amino)ethyl bromide (130 mg, 582 μmol, 1.5 eq.) was added to the reaction mixture and the reaction mixture was stirred at −78° C. for 20 min. and then warmed to room temperature. The reaction mixture was further stirred at room temperature overnight.

Workup

additionadded to a round-two-neck flask that
temperaturewas heated under vacuum
customflushed with nitrogen
stirringthe reaction mixture was stirred at −78° C. for 20 min.
temperaturewarmed to room temperature
stirringThe reaction mixture was further stirred at room temperature overnight

Sources & evidence

ORD record: ord-ba96b5922f344aa390be7703d7c677a2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921361B2

Reaction notes

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