Potassium Carbonate → HCID 86618449, compound

HRID 2098836Notes

Reaction equation

HRID 2098836 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]([CH2:23][CH2:24][CH2:25][NH2:26])(=[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][NH:26][CH2:25][CH2:24][CH2:23][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:4][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21949286HCID 21949286, compoundHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618449HCID 86618449, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (200 mg) in acetonitrile (10 mL) was added 3-methanesulfonyl-propylamine (86 mg) and potassium carbonate (317 mg) and the reaction heated at 80° C. for 16 h. After cooling to room temperature, the solvent was reduced in vacuo and the residue redissolved in dicholoromethane (20 mL). The solution was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL), aqueous brine solution (2×20 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(3-methanesulfonyl-propyl)-amine as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. dissolutionthe residue redissolved in dicholoromethane (20 mL)
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution (20 mL), aqueous brine solution (2×20 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-1bd5bb52c9d64171b58389afa1b3f514
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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