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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
ノート
印刷プレビュー

反応式

HRID 510370 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 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

生成物 1

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

試薬・触媒・溶媒 7

HCID 142844-(Dimethylamino)pyridine触媒
HCID 23938
Palladium
触媒
HCID 178521651HCID 178521651、化合物触媒
HCID 313Hydrochloric Acid溶媒
HCID 702Ethanol溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4db10e524ce4300b50de26441c49bd1
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096605B2

反応ノート

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