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

HRID 928570노트

반응식

HRID 928570 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[N:17]1([CH2:22][CH2:23][O:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[C:11]1([C:10]2[C:5]3[CH:4]=[N:3][C:2]([N:29]4[CH2:30][CH2:31][CH:26]([CH2:25][O:24][CH2:23][CH2:22][N:17]5[CH2:21][CH2:20][CH2:19][CH2:18]5)[CH2:27][CH2:28]4)=[N:7][C:6]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 821046552-Chloro-5-phenylthieno[2,3-d]pyrimidine

생성물 1

HCID 895794095-Phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine수율 26%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

2-Chloro-5-phenyl-thieno[2,3-d]pyrimidine (150 mg, 0.61 mmol), 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (293 mg, 0.92 mmol) and potassium carbonate (253 mg, 1.83 mmol) were combined in acetonitrile (2 mL) and heated in the microwave at 150° C. for 30 minutes. The reaction mixture was diluted with DCM (10 mL), washed with water (10 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by basic prep HPLC to afford 5-phenyl-2-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (67 mg). LCMS [M+H]+=423.2.

후처리

  1. washwashed with water (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by basic prep HPLC

출처 및 근거

ORD 기록
ord-e22e01285f2947b395f3a290516b9fdf
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

반응 노트

불러오는 중…