N-bromobutanimide → 6-bromo-7-(1-bromoethyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 58236Notes

Reaction equation

[Br:1][CH:2]([C:4]1[N:5]=[C:6]2[S:13][CH:12]=[C:11]([CH3:14])[N:7]2[C:8](=[O:10])[CH:9]=1)[CH3:3].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:9]1[C:8](=[O:10])[N:7]2[C:11]([CH3:14])=[CH:12][S:13][C:6]2=[N:5][C:4]=1[CH:2]([Br:1])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (16.2 g, 59.3 mmol) and N-bromosuccinimide (15.8 g, 89.0 mmol) in acetonitrile (500 mL) was stirred at 80° C., under nitrogen, overnight. After removal of acetonitrile in vacuum, the resulting solid was dissolved in methylene chloride, washed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine; and then the organic layers dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to provide the desired product (19.5 g, 93.4%). LCMS calculated for C9H9Br2N2OS (M+H)+: m/z=350.9. Found: 351.0.

Workup

customAfter removal of acetonitrile in vacuum
dissolutionthe resulting solid was dissolved in methylene chloride
washwashed with water, saturated Na2S2O3, saturated sodium bicarbonate, and brine
dry with materialand then the organic layers dried over sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2e150076aea6432abe0afac8d670f61d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434746B2

Reaction notes

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