Diisopropylethylamine → 4-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

HRID 2195061ノート

反応式

HRID 2195061 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]3[CH3:20])[N:11]=[C:10]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH3:26])[N:9]=2)=[CH:4][CH:3]=1.Br[C:28]1[C:33]([CH3:34])=[CH:32][C:31]([Br:35])=[CH:30][N:29]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.O>[Br:35][C:31]1[CH:32]=[C:33]([CH3:34])[C:28]([N:17]2[CH2:18][CH2:19][N:14]([C:12]3[CH:13]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:9]=[C:10]([N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH3:26])[N:11]=3)[C@H:15]([CH3:20])[CH2:16]2)=[N:29][CH:30]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 8176802,5-Dibromo-3-methylpyridineHCID 591683354-(4-Fluoro-phenyl)-6-(2-(R)-methyl-piperazin-1-yl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

生成物 1

HCID 591682874-[4-(5-bromo-3-methyl-pyridin-2-yl)-2-(R)-methyl-piperazin-1-yl]-6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

Heat a mixture of 4-(4-fluoro-phenyl)-6-(2-(R)-methyl-piperazin-1-yl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidine (400 mg, 1.13 mmol), 2,5-dibromo-3-methyl-pyridine (367 mg, 1.46 mmol), and DIEA (218 mg, 1.69 mmol) in DMA at 135° C. for 96 h. Dilute with water, extract with EtOAc, and wash with brine. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify the residue by flash column chromatography eluting with EtOAc-Hexanes (1:10) to afford the title compound as a white solid.

後処理

  1. temperatureHeat
  2. extractionextract with EtOAc
  3. washwash with brine
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash column chromatography
  7. washeluting with EtOAc-Hexanes (1:10)

出典と根拠

ORDレコード
ord-0827a4a2633244c4975e8dd1e90e2e49
出典データセット
uspto-grants-2012_12
特許番号
US08334382B2

反応ノート

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