Water → 2-[4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-N,N-dimethyl-isobutyramide

HRID 2365171Notes

Reaction equation

HRID 2365171 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][N:20]([CH3:32])[C:21](=[O:31])[C:22]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([CH3:24])[CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+].O>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:28]3[CH2:27][CH2:26][N:25]([C:22]([CH3:24])([CH3:23])[C:21]([N:20]([CH3:32])[CH3:19])=[O:31])[CH2:30][CH2:29]3)=[CH:4][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 22314768N,N-dimethyl-2-piperazin-1-yl-isobutyramideHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 591512572-[4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-N,N-dimethyl-isobutyramideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (146 mg, 0.42 mmol) in DMF (5 mL) were added N,N-dimethyl-2-piperazin-1-yl-isobutyramide (100 mg, 0.50 mmol), cesium carbonate (273 mg, 0.837 mmol) and water (23 μL, 1.26 mmol). The resulting mixture was stirred at RT for 17 h. The reaction mixture was loaded directly onto an Isolute® SCX-2 cartridge, washed with MeOH, then eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography to give the title compound as an off-white solid (131 mg, 67%).

Workup

  1. washwashed with MeOH
  2. washeluted with 2 M NH3 in MeOH
  3. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-9e4a01ab086e491b88bf5342164bc82f
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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