Potassium Carbonate → 7-Allyl-1-(5-hydroxyhexyl)-3-methylxanthine

HRID 1090620노트

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HRID 1090620 반응식
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:14])[N:8]([CH3:15])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].Cl[CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:23])[CH3:22])[C:9](=[O:14])[N:8]([CH3:15])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 824686-Chlorohexan-2-oneHCID 9739057-allyl-3-methyl-3,7-dihydro-1H-purine-2,6-dioneHCID 4311764Sodium borohydride

생성물 1

HCID 150238877-Allyl-1-(5-hydroxyhexyl)-3-methylxanthine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

To 11.8 g of 7-allyl-3-methyl-1-(5-oxyhexyl)-xanthine (prepared by alkylation of 7-allyl-3-methylxanthine with 1-chlorohexan-5-one in dimethylformamide in the presence of potassium carbonate at 100° C. for 5 hours; melting point: 71° C.), dissolved in 200 ml of ethanol, 1.5 g of sodium borohydride was added slowly under stirring at a temperature of max. 30° C. After stirring at room temperature for 6 hours the mixture was evaporated under reduced pressure. The residue was extractively worked up with dilute sodium hydroxide solution and with methylene chloride. The combined methylene chloride phases were washed with water, dried and evaporated under reduced pressure. The residue was purified by means of chromatography on silica gel (mobile phase: methylene chloride/ethanol/ammonia-solution (28%), volume ratio 8:2:0.2) and by recrystallization from methylene chloride/diethylether.

후처리

  1. custom30° C
  2. stirringAfter stirring at room temperature for 6 hours the mixture
  3. customwas evaporated under reduced pressure
  4. washThe combined methylene chloride phases were washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by means of chromatography on silica gel (mobile phase: methylene chloride/ethanol/ammonia-solution (28%), volume ratio 8:2:0.2) and by recrystallization from methylene chloride/diethylether

출처 및 근거

ORD 기록
ord-7f5b32a38f7b466daa990c97d7169274
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082845

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