Potassium Carbonate → 2-chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 391146Notes

Reaction equation

HRID 391146 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]([CH3:11])[NH:8][CH:7]([CH3:12])[CH2:6]1)(=[O:4])=[O:3].Br[CH2:14][C:15]1[S:23][C:22]2[C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:20][C:19]([Cl:30])=[N:18][C:17]=2[C:16]=1[CH3:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:30][C:19]1[N:20]=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:22]2[S:23][C:15]([CH2:14][N:8]3[C@H:9]([CH3:11])[CH2:10][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:6][C@@H:7]3[CH3:12])=[C:16]([CH3:31])[C:17]=2[N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 638725321-Methanesulfonyl-3,5-dimethylpiperazineHCID 783582564-(6-(Bromomethyl)-2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 866235702-chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-methanesulfonyl-3,5-dimethylpiperazine and 6-bromomethyl-2-chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine in acetonitrile was added potassium carbonate and the mixture refluxed overnight. After cooling to room temperature, the acetonitrile was removed under reduced pressure. DCM/sat. aq. NaHCO3 extraction and purification on silica gave 2-chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine.

Workup

  1. temperaturethe mixture refluxed overnight
  2. customthe acetonitrile was removed under reduced pressure
  3. extractionaq. NaHCO3 extraction and purification on silica

Sources & evidence

ORD record
ord-9798cca055504ae4822c5e7503a640c7
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

Loading…