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

HRID 2200686노트

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HRID 2200686 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c4e9b4f71d34749bae3ce3224f7e5b1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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