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

HRID 1093117ノート

反応式

HRID 1093117 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24872Rhodium chloride触媒HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-48a5766791e64aa1baa7066b2bde0cac
出典データセット
uspto-grants-2012_03
特許番号
US08129398B2

反応ノート

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