Potassium Carbonate → 5-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

HRID 2066536Notes

Reaction equation

HRID 2066536 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.[C:19]([O:23][C:24]([N:26]1[CH2:33][CH:32]2[CH:28]([CH2:29][NH:30][CH2:31]2)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.CCOC(C)=O>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH:28]2[CH:32]([CH2:31][N:30]([CH2:2][C:3]3[S:11][C:10]4[C:9]([N:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)=[N:8][C:7]([Cl:18])=[N:6][C:5]=4[CH:4]=3)[CH2:29]2)[CH2:33]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 581170715-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl esterYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (175 mg, 0.50 mmol) in DMF (5 mL) were added hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (160 mg, 0.754 mmol) and potassium carbonate (136 mg, 0.984 mmol). The resulting mixture was stirred at RT for 2 h, then diluted with water and EtOAc. The organic layer was isolated, then washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography to give the title compound as an off-white solid (218 mg, 90%).

Workup

  1. customThe organic layer was isolated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-51e1db2658a04375946e7e5a5c352df8
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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