Ammonium formate → 3-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200686ノート

反応式

HRID 2200686 の反応式
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:22])[N:12]([CH2:23][CH3:24])[C:11]=2[N:10]=[C:9]1[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:36])([F:35])[F:34])[CH:27]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:23]([N:12]1[C:11]2[N:10]=[C:9]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][C:33]([F:35])([F:36])[F:34])[CH:27]=3)[NH:8][C:16]=2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13]1=[O:22])[CH3:24]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 904023497-benzyl-3-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

生成物 1

HCID 904027233-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione収率 117.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

7-benzyl-3-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (0.62 g, 1.23 mmol, example 60) was dissolved in ethanol (20 mL); then the mixture was degassed and refilled with nitrogen three times. Ammonium formate (0.5 g, 7.94 mmol) and 10% Pd/C (30 mg) were added. The mixture was again degassed and refilled with nitrogen three times; then it was stirred at 80° C. overnight. The reaction was cooled and filtered. The filter cake was washed with methanol. The filtrate was concentrated to give 3-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (0.6 g, 100% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.61-7.57(t, 1H), 7.50(s, 1H), 7.40-7.38(dd, 1H), 7.31-7.29(d, 1H), 4.50(s, 1H), 3.95-3.85(m, 4H), 3.44-3.43(m, 2H), 1.73-1.66(t, 2H), 1.17-1.13(t, 3H). LCMS retention time 1.350 min; LCMS MH+ 415.

後処理

  1. customthen the mixture was degassed
  2. additionrefilled with nitrogen three times
  3. customThe mixture was again degassed
  4. additionrefilled with nitrogen three times
  5. temperatureThe reaction was cooled
  6. filtrationfiltered
  7. washThe filter cake was washed with methanol
  8. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-3c4e9b4f71d34749bae3ce3224f7e5b1
出典データセット
uspto-grants-2016_06
特許番号
US09359359B2

反応ノート

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