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

HRID 219743노트

반응식

HRID 219743 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[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39](S(C)(=O)=O)[N:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([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[CH2:23][CH2:22]4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:10]=3)[CH2:16][CH2:15]2)[N:38]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

5

반응물 3

HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidineHCID 690296093-[4-(2-tert-Butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-olHCID 178418339Butyllithium

생성물 1

HCID 690272064-{4-[3-(4-Benzyloxy-pyrimidin-2-yloxy)-propyl]-piperazin-1-yl}-2-tert-butyl-6-cyclopropyl-pyrimidine수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

0.5 g of 3-[4-(2-tert-Butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-ol (1.57 mmol) were dissolved in 5 ml of tetrahydrofuran. 1.5 ml of n-butyllithium (15% in hexane) were added to the mixture at 0° C. Stirring was continued for 30 min and then 0.45 g of 4-benzyloxy-2-methanesulfonyl-pyrimidine (1.7 mmol) dissolved in 5 ml of tetrahydrofuran were added. The reaction was stirred overnight at room temperature and for an additional 2 h at 40° 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 (0-3%) as eluent to yield 0.6 g of the title compound.

후처리

  1. additionwere added
  2. stirringThe reaction was stirred overnight at room temperature and for an additional 2 h at 40° 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-f94a99ec79cf4c3f8e1195824168c5cf
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202868B2

반응 노트

불러오는 중…