Cesium fluoride → Methyl 6-amino-2-(6-fluorobenzo[c][1,2,5]oxadiazol-5-yl)-5-methoxypyrimidine-4-carboxylate

HRID 1468973

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HRID 1468973 반응식
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14].[F:15][C:16]1[C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][C:19]2=[N:20][O:21][N:22]=[C:18]2[CH:17]=1.[F-].[Cs+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C.O>[NH2:1][C:2]1[N:7]=[C:6]([C:24]2[C:16]([F:15])=[CH:17][C:18]3=[N:22][O:21][N:20]=[C:19]3[CH:23]=2)[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14]

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 52270701Methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylateHCID 904038595-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]oxadiazole

생성물 1

HCID 90404596Methyl 6-amino-2-(6-fluorobenzo[c][1,2,5]oxadiazol-5-yl)-5-methoxypyrimidine-4-carboxylate수율 40.9%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 18373917Acetonitrile--water (1/1)용매

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온도
115 °C

실험 절차

Methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate (400 mg, 1.838 mmol), 5-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]oxadiazole (789 mg, 2.390 mmol), bis(triphenylphosphine)palladium(II) chloride (129 mg, 0.184 mmol), and cesium fluoride (558 mg, 3.68 mmol) were combined in 4 mL 1:1 ACN-water and heated at 115° C. for 30 min in a microwave reactor. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with saturated NaCl, dried, and evaporated. The product was purified by flash chromatography (SiO2, eluting with 5-30% ethyl acetate in dichloromethane) to provide the title compound (240 mg, 39%).

후처리

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated NaCl
  4. customdried
  5. customevaporated
  6. customThe product was purified by flash chromatography (SiO2, eluting with 5-30% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-095fa5622b374946892d12364e65bc40
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006250B2

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