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Diisopropylethylamine → 2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidine

HRID 510370
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HRID 510370 반응식
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:23])[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])=[C:6]2[N:5]=[C:4]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:3]=1.C(N(C(C)C)CC)(C)C>C(O)C.O1CCOCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.Cl.C([Mo](C=O)(C=O)(C=O)(C=O)C=O)=O.[Pd]>[CH3:23][C:9]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[C:13]=2[CH3:22])=[C:6]2[N:5]=[C:4]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:3]=[CH:2][N:7]2[N:8]=1
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참가 물질

10

반응물 2

HCID 81531DiisopropylethylamineHCID 867248677-chloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 712709062-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)-5-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidine수율 21%

시약·촉매·용매 7

HCID 142844-(Dimethylamino)pyridine촉매
HCID 23938
Palladium
촉매
HCID 178521651HCID 178521651, 화합물촉매
HCID 313Hydrochloric Acid용매
HCID 702Ethanol용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

To a suspension of 7-chloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidine (85 mg, 0.201 mmol) in ethanol (2 mL) and 1,4-dioxane (2 mL) were added hexaformylmolybdenum (27.1 mg, 0.100 mmol), Pd/C (1.0 mg, mmol) and DMAP (49 mg, 0.4 mmol) and diisopropylethylamine (26 mg, 0.2 mmol). The reaction mixture was irradiated (microwave) and stirred at 150° C. for 15 minutes. Reaction mixture was cooled down, diluted with ethyl acetate (30 mL) and 5% HCl solution. Two layers were separated. Organic layer was dried and concentrated to dryness. The crude product was purified to yield the titled compound (16 mg, 21%); LC/MS: MS (ES+) m/e 390 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.81 (m, 4H) 2.28 (s, 3H) 2.45-2.49 (m, 3H) 2.96 (s, 1H) 3.37-3.47 (m, 3H) 3.92 (br. s., 2H) 4.10 (s, 2H) 6.89 (d, J=7.33 Hz, 1H) 7.34 (s, 1H) 7.52 (s, 1H) 8.86 (d, J=7.33 Hz, 1H).

후처리

  1. customThe reaction mixture was irradiated (microwave)
  2. customReaction mixture
  3. temperaturewas cooled down
  4. customTwo layers were separated
  5. customOrganic layer was dried
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified

출처 및 근거

ORD 기록
ord-c4db10e524ce4300b50de26441c49bd1
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096605B2

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