Water → HCID 58548159, 화합물

HRID 2368227노트

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HRID 2368227 반응식
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[N:6]=1)=[O:4].Br[C:18]1[CH:19]=[N:20][CH:21]=[N:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O.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>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:18]2[CH:19]=[N:20][CH:21]=[N:22][CH:23]=2)=[N:9][CH:8]=[C:7]([CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)[N:6]=1)=[O:4]

참가 물질

9

반응물 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 783445-BromopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70097075HCID 70097075, 화합물

생성물 1

HCID 58548159HCID 58548159, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

A mixture of 3-amino-6-(tetrahydrofuran-3-yl)pyrazine-2-carboxylic acid methyl ester (300 mg, 1.34 mmol), 5-bromopyrimidine (299 mg, 1.88 mmol) and potassium carbonate (334 mg, 2.42 mmol) in xylene (15 ml) and water (51 μl, 2.82 mmol) was evacuated and vented with argon. Palladium (II) acetate (12.1 mg, 54 μmol) and xantphos (23.3 mg, 40 μmol) were added and the reaction mixture was stirred at 140° C. for 16 hr. The reaction mixture was cooled to r.t., poured into 50 ml ethyl acetate and extracted with water. The organic phase was washed with brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light solid (211 mg, 52%).

후처리

  1. customwas evacuated
  2. temperatureThe reaction mixture was cooled to r.t.
  3. extractionextracted with water
  4. washThe organic phase was washed with brine
  5. extractionthe aqueous layers were back-extracted with ethyl acetate
  6. customThe organic layers were dried
  7. customthe solvent was evaporated
  8. customThe product was obtained
  9. customafter purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-74df7c363dbe45a489a56e1824a8d755
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703768B2

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