Diisopropylethylamine → 6-chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 1641393ノート

反応式

HRID 1641393 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[C:5](Cl)=[C:4]([Cl:16])[N:3]=1.CCN(C(C)C)C(C)C.ClC1C(NC2C=C(OC(C)C)NN=2)=NC([NH:33][C@H:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)[CH3:35])=NC=1>CCO>[Cl:16][C:4]1[N:3]=[C:2]([NH:33][C@H:34]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)[CH3:35])[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[CH:5]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 509937282,5,6-trichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 178458654HCID 178458654、化合物

生成物 1

HCID 866248106-chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine収率 26.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

To a solution of 2,5,6-trichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 39; 2.0 g, 8.2 mmol) in absolute EtOH (40 ml) were added DIEA (2.5 ml) and (15)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 1.2 g, 8.2 mmol) and the resulting solution was heated to 140° C. for 12 hours. The mixture was partitioned between EtOAc and H2O, the organic layer was washed with brine and dried. The solvents were removed under reduced pressure to give an oil which was purified by Gilson (20-75% acetonitrile/H2O, 35 min) to give the titled compound as solid (762 mg). m/z: 383.

後処理

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe organic layer was washed with brine
  3. customdried
  4. customThe solvents were removed under reduced pressure
  5. customto give an oil which
  6. customwas purified by Gilson (20-75% acetonitrile/H2O, 35 min)

出典と根拠

ORDレコード
ord-60338ad174ce4776906f7f7e8acd1ae2
出典データセット
uspto-grants-2012_02
特許番号
US08114989B2

反応ノート

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