Potassium Carbonate → HCID 66617663, compound

HRID 2403425Notes

Reaction equation

Br[CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7](Cl)=[N:6][C:5]=2[CH:4]=1.Cl.[CH3:20][N:21]([CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)[S:22]([CH3:25])(=[O:24])=[O:23].[C:31](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][N:21]([CH:26]1[CH2:30][CH2:29][N:28]([CH2:2][C:3]2[S:11][C:10]3[C:9]([N:12]4[CH2:17][CH2:16][O:15][CH2:14][CH2:13]4)=[N:8][C:7]([CH3:31])=[N:6][C:5]=3[CH:4]=2)[CH2:27]1)[S:22]([CH3:25])(=[O:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (500 mg) and N-Methyl-N-pyrrolidin-3-yl-methanesulfonamide hydrochloride salt (370 mg) in acetonitrile (10 mL) was added potassium carbonate (490 mg). The reaction mixture was heated at 80° C. for 16 h and then allowed to cool to room temperature. The mixture was then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL) and the organic layer washed with brine (20 mL), dried (MgSO4), reduced in vacuo and purified on column chromatography to give N-methyl-N-[1-(2-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-pyrrolidin-3-yl]-methanesulfonamide as a pale yellow solid (395 mg).

Workup

temperatureto cool to room temperature
customThe mixture was then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
washthe organic layer washed with brine (20 mL)
dry with materialdried (MgSO4)
custompurified on column chromatography

Sources & evidence

ORD record: ord-2d7295eb9b1b4d60941d9fd7daaecb5d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802670B2

Reaction notes

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