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

HRID 1426408Notes

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-a68f5727e6544b53aa79530e36fe1cf6
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933069B2

Reaction notes

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