Sodium Carbonate → 2-(5-Chloro-2-fluorophenyl)-5-methylpyrimidin-4-amine

HRID 1522568ノート

反応式

HRID 1522568 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6](B(O)O)[CH:7]=1.Cl[C:13]1[N:18]=[C:17]([NH2:19])[C:16]([CH2:20]F)=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:13]2[N:18]=[C:17]([NH2:19])[C:16]([CH3:20])=[CH:15][N:14]=2)[CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 867043652-Chloro-5-fluoromethylpyrimidin-4-amine

生成物 1

HCID 674696142-(5-Chloro-2-fluorophenyl)-5-methylpyrimidin-4-amine

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

trans-Dichlorobis(triphenylphosphine)palladium (II) (1.179 g, 1.680 mmol), 5-chloro-2-fluorophenylboronic acid (6.1 g, 35.3 mmol), 2-chloro-5-fluoromethylpyrimidin-4-amine (2.411 g, 16.80 mmol), 2M Na2CO3 (8.40 mL, 16.80 mmol) were combined in dioxane (79 mL) and refluxed for 1 hour. The reaction was cooled, concentrated and the solids were suspended in brine (50 mL) and then extracted with EtOAc (20 mL). The layers were separated, the organics were dried over Na2SO4, filtered and concentrated to give a residue which was passed through a silica plug (12 g) to give 2-(5-chloro-2-fluorophenyl)-5-methylpyrimidin-4-amine which was without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (3H, d, J=0.76 Hz) 6.85 (2H, br. s.) 7.31 (1H, dd, J=10.61, 8.84 Hz) 7.46-7.55 (1H, m) 7.88 (1H, dd, J=6.57, 3.03 Hz) 8.06 (1H, d, J=0.76 Hz). ESI-MS: m/z 238.1 (M+H).

後処理

  1. temperaturerefluxed for 1 hour
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. extractionextracted with EtOAc (20 mL)
  5. customThe layers were separated
  6. dry with materialthe organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue which

出典と根拠

ORDレコード
ord-2a89c29a3d3b45e683111a3f6d19ae7b
出典データセット
uspto-grants-2015_07
特許番号
US09073918B2

反応ノート

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