Sodium Iodide → (S)-Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propyl ester

HRID 219709노트

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HRID 219709 반응식
[C:1]([C:5]1[N:10]=[C:9]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[I-].[Na+].[C:30]([O:33][CH2:34][C@@H:35]([CH3:38])[CH2:36]Br)(=[O:32])[CH3:31]>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:36][C@H:35]([CH3:38])[CH2:34][O:33][C:30](=[O:32])[CH3:31])[CH2:17][CH2:16]2)[CH:8]=[C:9]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10420167(R)-(-)-1-acetoxy-3-bromo-2-methyl-propaneHCID 666733902-tert-Butyl-4-cyclobutyl-6-(piperazin-1-yl)pyrimidine

생성물 1

HCID 131729779(S)-Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propyl ester수율 102.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

3.87 g of 2-tert-butyl-4-cyclobutyl-6-piperazin-1-yl-pyrimidine (14.1 mmol) were stirred in 30 ml of dimethylformamide at room temperature. 3.18 g of triethylamine (63.1 mmol), 0.235 g of sodium iodide (1.57 mmol), 2.96 g of (R)-(−)-1-acetoxy-3-bromo-2-methyl-propane (15.2 mmol) were added and the reaction mixture was stirred for 5 h at 95° C. The dimethylformamide was evaporated under reduced pressure. The residue was partitioned between 100 ml of dichloromethane and 100 ml of water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give a brownish oil (5.64 g).

후처리

  1. customThe dimethylformamide was evaporated under reduced pressure
  2. customThe residue was partitioned between 100 ml of dichloromethane and 100 ml of water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8ad93d4589f643a19d73bbb7382181e8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202868B2

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