Methyl Acrylate → methyl (E)-3-[2-(3-hydroxymethylphenyl)pyrimidin-5-yl]acrylate

HRID 2088406노트

반응식

HRID 2088406 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[K+]>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[OH:15][CH2:14][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[CH:3][C:2](/[CH:18]=[CH:17]/[C:16]([O:20][CH3:21])=[O:19])=[CH:7][N:6]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

9

반응물 4

HCID 7294Methyl AcrylateHCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 59484879(3-(5-Bromopyrimidin-2-yl)phenyl)methanol

생성물 1

HCID 58289762methyl (E)-3-[2-(3-hydroxymethylphenyl)pyrimidin-5-yl]acrylate

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

100 mg (0.38 mmol) of [3-(5-bromopyrimidin-2-yl)phenyl]methanol and 51 μl (0.56 mmol) of methyl acrylate are suspended in 2 ml of DMF, and 20 mg (0.075 mmol) of triphenylphosphine, 222 mg (2.26 mmol) of potassium acetate and 157 mg (0.57 mmol) of tetra-n-butylammonium chloride are added. The reaction mixture is degassed, flushed with argon, and 17 mg (0.075 mmol) of palladium(II) acetate are added under an argon atmosphere. The mixture is heated at 80° C. for 2 h. After cooling, water is added, during which a pale-grey precipitate forms. This is filtered off with suction, washed with water and dried in vacuo. The product is reacted further without further purification; yield: 111 mg; HPLC: Rt.=2.42 min (method A); LC-MS: 271 (M+H).

후처리

  1. customThe reaction mixture is degassed
  2. additionare added under an argon atmosphere
  3. temperatureAfter cooling
  4. filtrationThis is filtered off with suction
  5. washwashed with water
  6. customdried in vacuo
  7. customThe product is reacted further without further purification
  8. custom=2.42 min (method A)

출처 및 근거

ORD 기록
ord-71fd63246e7f491080246159a2936a3a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435986B2

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