Potassium Carbonate → HCID 86619260, compound

HRID 2403412Notes

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:18])=[N:6][C:5]=2[CH:4]=1.[CH3:19][N:20]([CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[S:21]([CH3:24])(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:18][C:7]1[N:8]=[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]2[S:11][C:3]([CH2:2][N:27]3[CH2:28][CH2:29][CH2:30][CH:26]3[CH2:25][N:20]([CH3:19])[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:4][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (0.50 g) and N-methyl-N-pyrrolidin-2-ylmethyl-methanesulfonamide (390 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 reaction mixture was then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give N-[1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-pyrrolidin-2-ylmethyl]-N-methyl-methanesulfonamide as a pale yellow solid (580 mg).

Workup

temperatureto cool to room temperature
customThe reaction mixture was then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
washThe combined organics were washed with brine (30 mL)
dry with materialdried (MgSO4)
custompurified by column chromatography

Sources & evidence

ORD record: ord-110c0f8e7a2b47358702a960f36a4f97
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802670B2

Reaction notes

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