Potassium Carbonate → 6-Amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

HRID 518984노트

반응식

HRID 518984 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1Br)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:18])[C:7](=[O:17])[NH:8][N:9]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH:19]1[CH2:21][CH2:20]1)[O:12][CH2:11][C:10]1[N:5]2[CH:6]([CH3:18])[C:7](=[O:17])[NH:8][N:9]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 86727335HCID 86727335, 화합물

생성물 1

HCID 867273366-Amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one수율 54%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

A mixture of 6-amino-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.500 g, 1.607 mmol), cyclopropylboronic acid (1.38 g, 16.07 mmol), K2CO3 (0.888 g, 6.43 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.262 g, 0.321 mmol) in water (10 mL) and dioxane (60 mL) was heated at 130° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 30-100% EtOAc in petroleum ether) to give 6-amino-7-cyclopropyl-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.235 g, 0.863 mmol, 54%). 1H NMR (DMSO-d6, 400 MHz): δ 10.71 (s 1H), 6.50 (s, 1H), 6.45 (s, 1H), 4.75 (brs, 2H), 4.45 (m, 3H), 1.60 (m, 1H), 1.31 (d, J=6.8 Hz, 3H), 0.83 (m, 2H), 0.46 (m, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationthe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 30-100% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-c7b2b8d3dde5497d87e42d64abe14383
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115151B2

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