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

HRID 28548

반응식

HRID 28548 반응식
[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

참가 물질

13

반응물 5

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

생성물 1

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

시약·촉매·용매 7

HCID 167845palladium(II) acetate촉매HCID 180Acetone용매HCID 702Ethanol용매HCID 962Water용매HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-110455df7da74eaf8850a0a690f33539
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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