Cesium carbonate → N4-(4-(4-ethylpiperazin-1-yl)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamine

HRID 58136노트

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HRID 58136 반응식
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][CH3:27])[CH:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:20]3[CH:21]=[C:22]([NH:26][CH3:27])[N:23]=[CH:24][N:25]=3)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 3094796-chloro-N-methylpyrimidin-4-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1180248134-(4-Ethylpiperazin-1-yl)-2-nitroaniline

생성물 1

HCID 118025883N4-(4-(4-ethylpiperazin-1-yl)-2-nitrophenyl)-N6-methylpyrimidine-4,6-diamine수율 29%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

A degassed mixture of 4-(4-ethylpiperazin-1-yl)-2-nitroaniline (2.1 g, 8.4 mmol), 6-chloro-N-methylpyrimidin-4-amine (Procedure 2A, step e; 1.2 g, 8.4 mmol), Pd2(dba)3 (1.54 g, 1.68 mmol), xantphos (1.94 g, 3.36 mmol) and Cs2CO3 (5.48 g, 16.8 mmol) in toluene (45 mL) was heated at 100° C. for 1 hour. The reaction was concentrated, and the residue was purified by flash chromatography on silica eluting with MeOH:DCM=1:40-1:20 to obtain the title compound (870 mg, yield: 29%). MS (ESI): 358 [M+H]+.

후처리

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica eluting with MeOH

출처 및 근거

ORD 기록
ord-9b079518ee454b17b0fab20d05cd8883
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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