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

HRID 1052152Notes

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-52199723e72843f88f6bde5384750342
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388195B2

Reaction notes

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