Potassium Carbonate → HCID 86619255, compound

HRID 390959Notes

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][S:20]([N:23]1[CH2:28][C@@H:27]([CH3:29])[NH:26][C@@H:25]([CH3:30])[CH2:24]1)(=[O:22])=[O:21].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:26]3[C@H:25]([CH3:30])[CH2:24][N:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH2:28][C@@H:27]3[CH3:29])=[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 (380 mg) and (3S,5R)-1-methanesulfonyl-3,5-dimethyl-piperazine (314 mg) in acetonitrile (10 mL) was added potassium carbonate (620 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 2-chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine.

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-d9cff9ddab924d4f90d7f2848b7116da
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383620B2

Reaction notes

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