Potassium Carbonate → (1S)-N-{[2-(2,6-diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]methyl}-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

HRID 1091928노트

반응식

HRID 1091928 반응식
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][N:10]([CH3:21])[C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[C:4]([CH3:22])[N:3]=1.[O:23]1[CH2:28]COCC1.[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH3:38])[C:32]=1B(O)O)[CH3:30].C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCOC(C)=O>[CH2:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH3:38])[C:32]=1[C:2]1[N:7]=[C:6]([O:23][CH3:28])[C:5]([CH2:9][N:10]([CH3:21])[C@@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[C:4]([CH3:22])[N:3]=1)[CH3:30]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 18437832(2,6-Diethylphenyl)boronic acidHCID 57531525(1S)-(2,4-Dichloro-6-methyl-pyrimidin-5-ylmethyl)methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine

생성물 1

HCID 57531359(1S)-N-{[2-(2,6-diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]methyl}-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a sealed tube containing (1S)-(2,4-dichloro-6-methyl-pyrimidin-5-ylmethyl)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine (3.4 g, 10.25 mmol) is added dioxane (40 mL), 2,6-diethylphenylboronic acid (3.65 g, 2.0 eq., 20.5 mmol) and K2CO3 (5.7 g, 4.0 eq., 41 mmol dissolved in 10 mL water) under a nitrogen atmosphere. Pd(PPh3)4 (5 mol %, 590 mg) is added and after sealing is allowed to react at 95° C. for 16 h. After cooling to room temperature, EtOAc (100 mL) and water (100 mL) is added and the organic layer is washed with sat. NaHCO3 (100 mL), brine (100 mL) and dried over Na2SO4. The crude sample is purified by SiO2 flash chromatography using hexanes:Et2O 5:1 with 1.0% triethylamine to recover the title compound as a colorless oil. [mass expected (429.60); mass found (429.33)]

후처리

  1. customto react at 95° C. for 16 h
  2. washthe organic layer is washed with sat. NaHCO3 (100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe crude sample is purified by SiO2 flash chromatography
  5. customto recover the title compound as a colorless oil

출처 및 근거

ORD 기록
ord-493c7bc89cb44fecae718a2c017789b0
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129395B2

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