1,2,3,4-Tetrahydroquinoline → 2-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine

HRID 75

반응식

HRID 75 반응식
Clc1ccnc(Cl)n1.c1ccc2c(c1)CCCN2>CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>Clc1nccc(N2CCCc3ccccc32)n1

참가 물질

7

반응물 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 775312,4-Dichloropyrimidine

생성물 1

HCID 227319232-Chloro-4-(1,2,3,4-tetrahydroquinolin-1-yl)pyrimidine수율 7.28%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

2,4-dichloropyrimidine (200 mg, 1.34 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (78 mg, 0.13 mmol), Tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) and Cesium carbonate (656 mg, 2.01 mmol) was added to a microwave vial. toluene (2 mL) was added. 1,2,3,4-tetrahydroquinoline (179 mg, 1.34 mmol) was added. Heated to 120ºC in microwave oven for 90min. Crude filtered through celite and then added to prepHPLC. 30-70% acetonitrile in water. Pure fractions pooled and then freezedried over night. Yielded 1-(2-chloropyrimidin-4-yl)-1,2,3,4-tetrahydroquinoline (24.00 mg, 7.28 %)

출처 및 근거

ORD 기록
ord-4dd72fee5c294abbb8cdefc25f205782
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
출처 보기

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