Hydrochloric Acid → 2-Chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine

HRID 28548

反応式

HRID 28548 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4](Cl)[N:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15](B(O)O)[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.C(O)C.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl.CC(C)=O.C(COC)OC>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[N:3]=1

参加物

13

反応物 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 823874-Pyrimidinamine, 2,6-dichloro-HCID 27357515-Chloro-2-methoxyphenylboronic acid

生成物 1

HCID 865946002-Chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine収率 15.5%

試薬・触媒・溶媒 7

HCID 167845palladium(II) acetate触媒HCID 180Acetone溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

Alternatively, to a mixture of 2,6-dichloro-pyrimidin-4-yl-amine (1.64 g, 10.0 mmol), 5-chloro-2-methoxy-phenyl boronic acid (1.84 g, 10.0 mmol), palladium (II) acetate (0.337 g, 1.0 mmol) and triphenylphosphine (0.786 g, 3.0 mmol) was added a solution of sodium carbonate (5.3 g, 50.0 mmol) in water (10 ml) followed by glyme (50 ml). The mixture was stirred under an argon atmosphere for 24 hours. After addition of acetone (50 ml), filtration and concentration of the filtrate provided the crude product which was treated with chloroform (50 ml) and stirred for 1 hour. Filtration provided a solid which was dissolved in ethanol (50 ml). A solution of hydrogen chloride in dioxane (4.0 M, 5 ml) was added and volatiles were evaporated under reduce pressure. The residue was treated with ethyl acetate (25 ml) and stirred for 2 hours. Filtration provided the hydrochloride salt of 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-4-yl-amine (0.42 g, 14% yield).

後処理

  1. customprovided the crude product which
  2. stirringstirred for 1 hour
  3. filtrationFiltration
  4. customprovided a solid which
  5. customvolatiles were evaporated
  6. additionThe residue was treated with ethyl acetate (25 ml)
  7. stirringstirred for 2 hours
  8. filtrationFiltration

出典と根拠

ORDレコード
ord-110455df7da74eaf8850a0a690f33539
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

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