Water → [1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-methyl-carbamic acid tert-butyl ester

HRID 2365183Notes

Reaction equation

HRID 2365183 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.O.[C:20]([O:24][C:25](=[O:34])[N:26]([CH3:33])[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:20]([O:24][C:25](=[O:34])[N:26]([CH:27]1[CH2:28][CH2:29][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)[CH2:31][CH2:32]1)[CH3:33])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 59151274[1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-methyl-carbamic acid tert-butyl esterYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (85 mg, 0.244 mmol) in DMF (2 mL) were added water (13 μL), methyl-piperidin-4-yl-carbamic acid tert-butyl ester (105 mg, 0.489 mmol) and cesium carbonate (159 mg, 0.489 mmol). The resulting mixture was stirred at RT for 18 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH. The resultant residue was purified by column chromatography to give the title compound as a pale brown solid (73 mg, 62%).

Workup

  1. washwashed with MeOH
  2. washthen eluted with 2 M NH3 in MeOH
  3. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c881f4789484d6ab3fed1eeba651ea7
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

Loading…