Potassium Carbonate → HCID 59151318, compound

HRID 2365184Notes

Reaction equation

HRID 2365184 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.Cl.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][C@H:28]1[CH:33]([CH3:35])[CH3:34])=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(Cl)Cl>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([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]([Cl:18])=[N:6][C:5]=3[CH:4]=2)[CH2:29][C@H:28]1[CH:33]([CH3:35])[CH3:34])=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 45072240tert-Butyl (2R)-2-(propan-2-yl)piperazine-1-carboxylate--hydrogen chloride (1/1)HCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59151318HCID 59151318, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (100 mg, 0.29 mmol) in DMF (3 mL) were added (R)-2-isopropyl-piperazine-1-carboxylic acid tert-butyl ester hydrochloride (87 mg, 0.33 mmol) and potassium carbonate (124 mg, 0.90 mmol). The resulting mixture was stirred at RT for 18 h, then diluted with water and DCM. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a white solid (139 mg, 97%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-47078f88e53c466bbad9f2c3b32af1dd
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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