Ethanol → 4-(2-(Trifluoromethyl)phenyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1871359ノート

反応式

HRID 1871359 の反応式
Cl[C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C(OCC)(=O)C.C1C=CC=CC=1>[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 154284084-Chloro-7-mesityl-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 186912984-(2-(Trifluoromethyl)phenyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-chloro-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine (425 mg, prepared as described by Y. L. Chen in Patent Application WO94/13676), 2-(trifluoromethyl)phenylboronic acid (310 mg) tetrakis(triphenylphoshine)palladium(0) (50 mg), 1M aqueous sodium carbonate (2 mL), ethanol (0.75 mL) and benzene (6 mL) was refluxed for 6 hr. The cooled mixture was diluted with ethyl acetate and the aqueous layer was removed. The organic layer was washed with 1N aqueous sodium hydroxide, and brine, dried, and concentrated in vacuo. The crude reaction product was chromatographed on silica gel using ethyl acetate/hexanes (1:3) as eluent. The title compound was obtained as a glass (300 mg) that crystallized on trituration with ether to give crystals, mp 176.5-177.5°. Elemental Analysis: Calcd. for C22H24N3F3 : C, 70.91: H, 5.71; N, 9.92. Found: C, 70.69; H, 5.72; N, 9.84.

後処理

  1. temperaturewas refluxed for 6 hr
  2. customthe aqueous layer was removed
  3. washThe organic layer was washed with 1N aqueous sodium hydroxide, and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crude reaction product
  7. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-9337870be9ca42c8b6439136e492e430
出典データセット
uspto-grants-2000_08
特許番号
US06103737

反応ノート

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