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

HRID 1522568노트

반응식

HRID 1522568 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2a89c29a3d3b45e683111a3f6d19ae7b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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