2-Methylsulfonyl-4-benzyloxy-pyrimidine → 4-{4-[3-(4-Benzyloxy-pyrimidin-2-yloxy)-propyl]-piperazin-1-yl}-2-tert-butyl-6-cyclobutyl-pyrimidine

HRID 219736노트

반응식

HRID 219736 반응식
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][N:41]=[C:40](S(C)(=O)=O)[N:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][N:41]=[C:40]([O:20][CH2:19][CH2:18][CH2:17][N:14]2[CH2:13][CH2:12][N:11]([C:9]3[CH:8]=[C:7]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:10]=3)[CH2:16][CH2:15]2)[N:39]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

참가 물질

5

반응물 3

HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidineHCID 690262333-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-olHCID 178418339Butyllithium

생성물 1

HCID 690276004-{4-[3-(4-Benzyloxy-pyrimidin-2-yloxy)-propyl]-piperazin-1-yl}-2-tert-butyl-6-cyclobutyl-pyrimidine수율 53.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

0.9 g of 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-ol (2.71 mmol) were dissolved in 20 ml of tetrahydrofuran. 2.75 ml of n-butyllithium (15% in hexane) were added at 0° C. The reaction mixture was stirred for 30 min. 0.79 g of 4-benzyloxy-2-methanesulfonyl-pyrimidine (3.0 mmol) dissolved in 10 ml of tetrahydrofuran were then added. The reaction mixture was stirred overnight at room temperature and for an additional 6 h at 60° C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (1.5%) as eluent to yield 0.75 g of the title compound.

후처리

  1. additionwere then added
  2. stirringThe reaction mixture was stirred overnight at room temperature and for an additional 6 h at 60° C
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-963166b782764b7a8233dbb6ed80b0fa
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202868B2

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