Water → 6-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyrazin-2-one

HRID 2194403

반응식

HRID 2194403 반응식
C([O:4][C:5]1[CH:10]=[N:9][CH:8]=[C:7]([N:11]2[CH:15]=[C:14]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[N:13]=[C:12]2[CH3:25])[N:6]=1)C=C.C1([SiH3])C=CC=CC=1.O>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]([C:17]#[C:16][C:14]2[N:13]=[C:12]([CH3:25])[N:11]([C:7]3[NH:6][C:5](=[O:4])[CH:10]=[N:9][CH:8]=3)[CH:15]=2)[CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 12752PhenylsilaneHCID 668656112-Allyloxy-6-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyrazine

생성물 1

HCID 668653666-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyrazin-2-one수율 45.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 75 mg (0.214 mmol) 2-Allyloxy-6-[4-(3-chloro-phenylethynyl)-2-methyl imidazol-1-yl]-pyrazine in 5 ml of methylene chloride was degassed with argon. Then 0.052 ml (0.428 mmol) of phenyl silane and 2.5 mg (0.002 mmol) of tetrakis(triphenyl-phosphine)palladium were added and the mixture was stirred for 1 h at room temperature. Then water (1 ml) was added and the mixture was vigourously stirred for 5 min., diluted with 10 ml of methylene chloride and the organic phase was washed with water and brine, dried over magnesium sulfate and concentrated. The obtained solid was triturated with benzene to remove impurities (triphenylphosphine oxide), filtered and dried to yield 30 mg (0.097 mmol, 45%) of the title compound as a white crystalline solid, MS: m/e=311.1, 313.1 (M+H+)

후처리

  1. stirringthe mixture was vigourously stirred for 5 min.
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained solid was triturated with benzene
  6. customto remove impurities (triphenylphosphine oxide)
  7. filtrationfiltered
  8. customdried

출처 및 근거

ORD 기록
ord-3d334f4b4c1f4ce09d63fa3ca7a79fdd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334287B2

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