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

HRID 928586노트

반응식

HRID 928586 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-01635be38be94c24bb3a83e9a48197a3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

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