Methyl Acrylate → methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate

HRID 705787노트

반응식

HRID 705787 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N:4]1[CH:3]=[C:2](/[CH:10]=[CH:9]/[C:8]([O:12][CH3:13])=[O:11])[CH:7]=[N:6][CH:5]=1

참가 물질

6

반응물 2

HCID 7294Methyl AcrylateHCID 783445-Bromopyrimidine

생성물 1

HCID 18470237methyl (2E)-3-(pyrimidin-5-yl)prop-2-enoate수율 66.4%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-bromopyrimidine (22.82 g, 144 mmol), methyl 2-propenoate (14.83 g, 172 mmol), palladium(II) acetate (0.322 g, 1.435 mmol), tri-o-tolylphosphine (0.874 g, 2.87 mmol), and TEA (32.0 g, 316 mmol) in DMF (100 mL) was heated at 130° C. under N2 for 7 h. After cooling, the reaction mixture was partitioned between water (200 mL) and DCM (200 mL). The organic phase was collected, washed with water (200 mL×4), brine, dried over sodium sulphate, and concentrated in vacuo to give the crude title compound as a pale yellow solid (18.4 g, 95 mmol, 66.4%). LCMS: rt=1.01 min, [M+H+]=165

후처리

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water (200 mL) and DCM (200 mL)
  3. customThe organic phase was collected
  4. washwashed with water (200 mL×4), brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d7cf5728afb34bb1934b3fcaff7f150d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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