Thiophene → HCID 178480440, 화합물

HRID 256666

반응식

HRID 256666 반응식
Br.Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[OH:20])[N:13]=[C:12]2[NH:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:6][CH:5]=1.S1C=CC=[CH:29]1.C([O-])(=O)C.[K+].[H][H]>CO.[Pd]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[OH:20])[N:13]=[C:12]2[NH:21][CH:22]2[CH2:23][CH2:24][N:25]([CH3:29])[CH2:26][CH2:27]2)=[CH:6][CH:5]=1

참가 물질

8

반응물 5

HCID 8030ThiopheneHCID 517044Potassium AcetateHCID 178418361HCID 178418361, 화합물HCID 178419280HCID 178419280, 화합물HCID 178486302HCID 178486302, 화합물

생성물 1

HCID 178480440HCID 178480440, 화합물수율 56%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매2회

실험 절차

A mixture of 3 parts of poly(oxymethylene), 5 parts of 7-[(4-fluorophenyl)methyl]-8-(4-piperidinylamino)-7H-purin-6-ol dihydrobromide, 1 part of a solution of thiophene in methanol 4%, 5 parts of potassium acetate and 120 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and the whole was treated with sodium carbonate. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 2 parts (56%) of 7-[(4-fluorophenyl)methyl]-8-[(1-methyl-4-piperidinyl)amino] -7H-purin-6-ol; mp. 255.6° C. (compound 139).

후처리

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionthe whole was treated with sodium carbonate
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from acetonitrile
  13. filtrationThe product was filtered off
  14. customdried

출처 및 근거

ORD 기록
ord-c54705a1b31a42c2816ada1141e4e2fc
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258380

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