Acetaldehyde → 3-Cyclopropylmethyl-8-[4-(ethyl-amino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

HRID 720688노트

반응식

HRID 720688 반응식
[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)[NH:10][C:9]=3[C:8](=[O:22])[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:6]2=[O:31])[CH2:3][CH2:2]1.[CH:32](=O)[CH3:33]>[Pd].O1CCCC1>[CH:1]1([CH2:4][N:5]2[C:13]3[N:12]=[C:11]([CH2:14][C:15]4[CH:16]=[CH:17][C:18]([NH:21][CH2:32][CH3:33])=[CH:19][CH:20]=4)[NH:10][C:9]=3[C:8](=[O:22])[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:6]2=[O:31])[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 177AcetaldehydeHCID 218917373-Cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione

생성물 1

HCID 218918193-Cyclopropylmethyl-8-[4-(ethyl-amino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione수율 62.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 10% palladium on carbon (0.10 g) in tetrahydrofuran (50 mL) was added 3-cyclopropylmethyl-8-[4-aminobenzyl]-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione (prepared as described in example 64, step 1) (0.21 g, 0.50 mmol) and acetaldehyde (72.6 μL, 1.3 mmol). The mixture was shaken under an atmosphere of hydrogen at 1 atmosphere pressure and ambient temperature for 3 days. The catalyst was removed by filtration through celite, washing the filter pad through with tetrahydrofuran and methanol. The combined filtrate was concentrated in vacuo and the residue purified by chromatography using silica eluted with 1:1 hexanes/ethyl acetate. Concentration of the appropriate fractions gave the product as a colorless solid (0.14 g, 62%). MS, m/z(M+H)=553.

후처리

  1. customThe catalyst was removed by filtration through celite
  2. washwashing the filter pad through with tetrahydrofuran and methanol
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. customthe residue purified by chromatography
  5. washeluted with 1:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-d7b4319582c34293b3c5c8e64c59603d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135475B2

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