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Methanol → 7-Demethylated M1 pentoxifylline (M7)

HRID 1814974
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HRID 1814974 반응식
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([OH:24])[CH3:23])[C:13](=[O:25])[N:12]([CH3:26])[C:11]=2[N:10]=[CH:9]1)C1C=CC=CC=1.CO.[H][H]>[Pd].C(O)(=O)C>[OH:24][C@H:22]([CH3:23])[CH2:21][CH2:20][CH2:19][CH2:18][N:14]1[C:15](=[O:17])[C:16]2[NH:8][CH:9]=[N:10][C:11]=2[N:12]([CH3:26])[C:13]1=[O:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 887MethanolHCID 9885048(R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 536898477-Demethylated M1 pentoxifylline (M7)수율 66.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid
용매

실험 절차

A mixture of (R)-7-benzyl-1-(5-hydroxyhexyl)-3-methylxanthine (33.7 g, 84.7 mmol), methanol (60 ml), acetic acid (60 ml), and 10% palladium on carbon (6 g) was treated with hydrogen gas (40 psi) on a Parr shaker. After 14 hours, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol/ethyl acetate to provide (R)-1-(5-hydroxyhexyl)-3-methylxanthine (15 g).

후처리

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-7734cbdae32342f49e5675b911f7a545
출처 데이터셋
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06878715B1

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