Methanol → HCID 15023901, compound

HRID 2420083Notes

Reaction equation

HRID 2420083 reaction equation
[CH2:1]([N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[CH:13]=[N:12][C:11]=2[N:10]([CH3:25])[C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CO.[BH4-].[Na+]>C(O)(=O)C>[CH2:1]([N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([OH:24])[CH3:23])[CH:13]=[N:12][C:11]=2[N:10]([CH3:25])[C:8]1=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 12902751HCID 12902751, compound

Product 1

HCID 15023901HCID 15023901, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

25 g of 1-n-hexyl-3-methyl-7-(5-oxohexyl)-xanthine, 100 ml of methanol and 1.0 g sodium borohydride are stirred at ambient temperature for 30 minutes. The mixture is then acidified with crystalline acetic acid to a pH-value of 5. The alcohol is evaporated and the residue is dissolved in 200 ml of methylene chloride and washed with 2N sodium hydroxide solution and with water. After evaporation of the methylene chloride, the product is recrystallised from 250 ml of diisopropyl ether. The 1-n-hexyl-3-methyl-7-(5-hydroxyhexyl)-xanthine obtained (88% of theory) has a melting point of 68° to 69° C.

Workup

  1. customThe alcohol is evaporated
  2. dissolutionthe residue is dissolved in 200 ml of methylene chloride
  3. washwashed with 2N sodium hydroxide solution and with water
  4. customAfter evaporation of the methylene chloride
  5. customthe product is recrystallised from 250 ml of diisopropyl ether

Sources & evidence

ORD record
ord-471085a30f6f450b8562ef32a4ebc1e8
Source dataset
uspto-grants-1978_08
Patent number
US04108995

Reaction notes

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