Cesium carbonate → 2-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine

HRID 1875447노트

반응식

HRID 1875447 반응식
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[NH:7][N:6]=1.Cl[C:19]1[N:24]=[C:23]([NH2:25])[C:22]([N+:26]([O-:28])=[O:27])=[C:21]([NH2:29])[N:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>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].CN(C=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:19]2[N:20]=[C:21]([NH2:29])[C:22]([N+:26]([O-:28])=[O:27])=[C:23]([NH2:25])[N:24]=2)[N:6]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59177864HCID 59177864, 화합물HCID 178505620HCID 178505620, 화합물

생성물 1

HCID 591778732-[3-(2-Fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A solution of 600 mg (2.64 mmol) of 3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridine from example 4A, 501 mg (2.64 mmol) of 2-chloro-5-nitropyrimidine-4,6-diamine [Bitterli et al., Helv. Chim. Acta 1951, 34, 835], 48.4 mg (0.053 mmol) of tris(dibenzylideneacetone)dipalladium, 75.5 mg (0.158 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 1.20 g (3.70 mmol) of cesium carbonate in a degassed mixture of 10 ml of toluene and 10 ml of DMF is heated at 90° C. for 4 h. Cooling to room temperature is followed by filtration with suction and washing with THF. The solid is stirred with 100 ml of water and again filtered off with suction. 572 mg (57% of theory) of the desired compound are obtained.

후처리

  1. temperatureCooling to room temperature
  2. filtrationis followed by filtration with suction
  3. washwashing with THF
  4. filtrationagain filtered off with suction

출처 및 근거

ORD 기록
ord-93104f7e0b9c4c899b6843c9df33bdd6
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309551B2

반응 노트

불러오는 중…