Water → HCID 58548159、化合物

HRID 467630ノート

反応式

HRID 467630 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

HCID 58548159HCID 58548159、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 7237O-Xylene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2f90a6c0fb4242769f9f4bd04fa656a0
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

反応ノート

読み込み中…