Water → 2-{(R)-3-[4-(2-tert-Butyl-6-cyclobutylpyrimidin-4-yl)-piperazin-1-yl]-2-methylpropoxy}-4-benzoyloxypyrimidin

HRID 219753노트

반응식

HRID 219753 반응식
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][OH:20])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CS([C:35]1[N:40]=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:38]=[CH:37][N:36]=1)(=O)=O.[OH2:49]>O1CCCC1>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][O:20][C:35]3[N:40]=[C:39]([O:41][C:42](=[O:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:38]=[CH:37][N:36]=3)[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 962Water2회HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidineHCID 69025424(R)-3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-olHCID 178418339Butyllithium

생성물 1

HCID 690262242-{(R)-3-[4-(2-tert-Butyl-6-cyclobutylpyrimidin-4-yl)-piperazin-1-yl]-2-methylpropoxy}-4-benzoyloxypyrimidin

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1.05 g of (R)-3-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-ol (3.02 mmol) were dissolved in 8 ml of tetrahydrofuran. At 0° C., 1.71 ml (3.37 mmol) of n-butyllithium (2 M in pentane) were added within 15 minutes. 0.85 g of 2-methylsulfonyl-4-benzyloxy-pyrimidine (3.21 mmol), dissolved in 5 ml of tetrahydrofurane, were added. Stirring continued for 16 h at room temperature. By cooling with, 2 ml of water were added. The obtained mixture was poured into 15 ml of water and extracted three times with 15 ml of diethyl ether each. The organic layers were combined, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2 to yield 0.83 g of the product.

후처리

  1. additionwere added
  2. additionwere added
  3. extractionextracted three times with 15 ml of diethyl ether each
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2

출처 및 근거

ORD 기록
ord-00ac25f94b0e43e1a6cf2a87cf0a35d2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202868B2

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