Potassium Carbonate → 6-Bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928586Notes

Reaction equation

HRID 928586 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16][C:17]1[S:26][C:20]2[N:21]=[C:22](Cl)[N:23]=[CH:24][C:19]=2[C:18]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[Br:16][C:17]1[S:26][C:20]2[N:21]=[C:22]([N:13]3[CH2:14][CH2:15][CH:10]([CH2:9][O:8][CH2:7][CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:11][CH2:12]3)[N:23]=[CH:24][C:19]=2[C:18]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 895794776-Bromo-2-chloro-5-phenyl-thieno[2,3-d]pyrimidine

Product 1

HCID 895794806-Bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidineYield 42.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine (0.567 g, 1.74 mmol), 6-bromo-2-chloro-5-phenyl-thieno[2,3-d]pyrimidine (0.554 g, 2.61 mmol) and potassium carbonate (7.21 g, 7.7 mmol) were combined and heated in acetonitrile for 30 minutes to 150° C. in the microwave. The reaction mixture was diluted with DCM, washed with water, dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with DCM—92/8/2 DCM/MeOH/NH4OH gradient to afford 6-bromo-5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (374 mg). LCMS [M+H]+=501.1

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by flash chromatography
  5. washeluting with DCM—92/8/2 DCM/MeOH/NH4OH gradient

Sources & evidence

ORD record
ord-01635be38be94c24bb3a83e9a48197a3
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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