Sodium Iodide → 6-bromo-2-(pyrrolidin-1-ylmethyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1409001Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Br:14][C:15]1[S:23][C:22]2[C:21](=[O:24])[NH:20][C:19]([CH2:25]Cl)=[N:18][C:17]=2[CH:16]=1>CN(C)C=O>[Br:14][C:15]1[S:23][C:22]2[C:21](=[O:24])[NH:20][C:19]([CH2:25][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:18][C:17]=2[CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of pyrrolidine (2.2 mL), potassium carbonate (2.5 g), sodium iodide (134 mg) and N,N-dimethylformamide (40 mL) was added 6-bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one (2.5 g), and the mixture was stirred at 70° C. for 30 min. Insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was washed with a small amount of ethyl acetate to give the title compound (1.5 g) as a pale-yellow solid. The filtrate was purified by basic silica gel column chromatography (methanol/ethyl acetate) to give the title compound (0.87 g) as a pale-yellow solid. The total yield of the title compound was 2.37 g.

Workup

customInsoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
washthe residue was washed with a small amount of ethyl acetate

Sources & evidence

ORD record: ord-67733bb8a15e451594bc06741a77eb72
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921354B2

Reaction notes

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