Sodium Carbonate → 6-(4-Amino-3,5-dimethylphenyl)-3-methylpyrimidin-4(3H)-one

HRID 237586

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HRID 237586 반응식
[CH3:1][C:2]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[C:5]([CH3:18])[C:3]=1[NH2:4].Cl[C:20]1[N:25]=[CH:24][N:23]([CH3:26])[C:22](=[O:27])[CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[NH2:4][C:3]1[C:5]([CH3:18])=[CH:6][C:7]([C:20]2[N:25]=[CH:24][N:23]([CH3:26])[C:22](=[O:27])[CH:21]=2)=[CH:8][C:2]=1[CH3:1]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 43664716-Chloro-3-methylpyrimidin-4(3H)-oneHCID 567377242,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

생성물 1

HCID 866972496-(4-Amino-3,5-dimethylphenyl)-3-methylpyrimidin-4(3H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

In a microwave vial 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.6 g) and 6-chloro-3-methylpyrimidin-4(3H)-one (3 g) are suspended in N,N-dimethylformamide (30 mL) and Na2CO3 (26 mL of a 2M aqueous solution). The mixture is purged for 5 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (508 mg) is added, the vial is sealed and the mixture is stirred at 65° C. for 12 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated to give the title compound. Yield: 2.6 g; LC (method 11): tR=0.71 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

후처리

  1. customThe mixture is purged for 5 minutes with argon
  2. addition[1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (508 mg) is added
  3. customthe vial is sealed
  4. temperatureAfter cooling to room temperature the mixture
  5. customis Partitioned between water and ethyl acetate
  6. extractionThe aqueous phase is extracted twice with ethyl acetate
  7. washthe combined organic phases are washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvents are evaporated

출처 및 근거

ORD 기록
ord-c31715c430bd41598881d2f21c3a7fac
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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