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Methanol → 7-Demethylated M1 pentoxifylline (M7)

HRID 1814974
Notes
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Reaction equation

HRID 1814974 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 176
Acetic Acid
Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7734cbdae32342f49e5675b911f7a545
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06878715B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes