Triethylamine → 2-Cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928592노트

반응식

HRID 928592 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.C(N(CC)CC)C.Cl[C:24]1[C:25]2[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])=[CH:34][S:33][C:26]=2[N:27]=[C:28]([CH:30]2[CH2:32][CH2:31]2)[N:29]=1>C(O)C>[CH:30]1([C:28]2[N:29]=[C:24]([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)[C:25]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:34][S:33][C:26]=3[N:27]=2)[CH2:32][CH2:31]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 895793654-Chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine

생성물 1

HCID 895796182-Cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine수율 19%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine (0.10 g, 0.47 mmol), triethylamine (0.089 mL, 0.63 mmol) and 4-chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine (0.10 g, 0.32 mmol) were combined and heated to 50° C. in ethanol (10 mL) overnight. The solvent was removed at reduced pressure. The residue was taken up in DCM (20 mL), washed with water (20 mL) and the organic dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of DCM to 90/10/1 DCM/MeOH/NH4OH to afford 2-cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (0.03 g). LCMS: purity 100%, RT=3.62 min, M+1=493.1

후처리

  1. customThe solvent was removed at reduced pressure
  2. washwashed with water (20 mL)
  3. dry with materialthe organic dried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with a gradient of DCM to 90/10/1 DCM/MeOH/NH4OH

출처 및 근거

ORD 기록
ord-29d286d192074e6e95baeb6e9661b0f7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290511B2

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