Potassium Carbonate → 2-Chloro-6-[(S)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066477Notes

Reaction equation

HRID 2066477 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.[CH2:19]1[NH:24][CH2:23][CH2:22][N:21]2[CH2:25][CH2:26][CH2:27][C@@H:20]12.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)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:24]3[CH2:23][CH2:22][N:21]4[CH2:25][CH2:26][CH2:27][C@H:20]4[CH2:19]3)=[CH:4][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonaneHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 581170982-Chloro-6-[(S)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (150 mg, 0.43 mmol) in DMF (4 mL) were added (S)-octahydro-pyrrolo[1,2-a]pyrazine (81 mg, 0.642 mmol) and potassium carbonate (117 mg, 0.847 mmol). The resulting mixture was stirred at RT for 17 h, then concentrated in vacuo. The resulting residue was triturated with water to give the title compound as an off-white solid (130 mg, 77%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was triturated with water

Sources & evidence

ORD record
ord-56c3bd040cee4f12bd86b9d0b1d24274
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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