Nitrogen → Ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1093117노트

반응식

HRID 1093117 반응식
C([O:4][C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)[N:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C=C.N#N>C(O)CC.[Rh](Cl)(Cl)Cl>[CH2:25]([O:24][C:6]1[C:5](=[O:4])[NH:10][C:9]([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][OH:18])[CH2:15][CH2:16]2)=[N:8][C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 2

HCID 947NitrogenHCID 57904733Ethyl 6-(allyloxy)-5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)pyrimidine-4-carboxylate

생성물 1

HCID 136061319Ethyl 5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate수율 76%

시약·촉매·용매 2

HCID 24872Rhodium chloride촉매HCID 10311-Propanol용매

반응 조건

온도
100 °C

실험 절차

A solution of ethyl 6-(allyloxy)-5-(benzyloxy)-2-(4-(hydroxymethyl)piperidin-1-yl)pyrimidine-4-carboxylate (1.206 g, 2.82 mmol) in n-propanol (10 mL) was sparged with N2. Rhodium(III) chloride (0.030 g, 0.141 mmol) was added and the resulting mixture was stirred overnight at 100° C. The mixture was cooled to room temperature and partitioned between water and CH2Cl2. The organic phase was dried (Na2SO4), filtered and concentrated to give a yellow solid that was triturated with Et2O. The product was collected by filtration to give the title compound as a white solid (0.8252 g, 76% yield). 1H NMR (300 MHz, CDCl3) δ: 7.43 (2H, d, J=7.3 Hz), 7.37-7.29 (3H, m), 5.05 (2H, s), 4.46 (2H, d, J=13.1 Hz), 4.31 (2H, q, J=7.1 Hz), 3.44 (2H, d, J=5.8 Hz), 2.94-2.88 (2H, m), 1.74 (2H, d, J=13.1 Hz), 1.73-1.66 (1H, m), 1.29 (3H, t, J=7.2 Hz), 1.28-1.22 (2H, m). LCMS (M+H) calcd for C20H26N3O5: 388.18; found: 388.23.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water and CH2Cl2
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customthat was triturated with Et2O
  8. filtrationThe product was collected by filtration

출처 및 근거

ORD 기록
ord-48a5766791e64aa1baa7066b2bde0cac
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129398B2

반응 노트

불러오는 중…