Water → 4-(5-phenylpentylthio)-1-beta-D-ribofuranosyl-pyrazolo[3,4-d]pyrimidine

HRID 1155040Notes

Reaction equation

HRID 1155040 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH:13][C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([C@@H:23]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]3[OH:25])[N:21]=[CH:22][C:15]=12.C(=O)(O)[O-].[K+].O>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C@@H:23]4[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]4[OH:25])[N:21]=[CH:22][C:15]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516893Potassium Bicarbonate2×HCID 5191731-Chloro-5-phenylpentaneHCID 178521072HCID 178521072, compound

Product 1

HCID 541486874-(5-phenylpentylthio)-1-beta-D-ribofuranosyl-pyrazolo[3,4-d]pyrimidineYield 9.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 5-phenylpentyl chloride (1.3 g) was added to a stirred solution of 4-mercapto-1-β-D-ribofuranosylpyrazolo [3,4-d]pyrimidine (2.0 g) and potassium bicarbonate (0.7 g) in N,N-dimethylformamide. The reaction mixture was heated on a steam bath for 25 hours. An additional 0.7 g of potassium bicarbonate was added and after heating for 1 hour more, the mixture was poured into water. The cooled aqueous mixture was extracted with chloroform. The chloroform soluble material was chromatographed on a silica gel column. The fractions containing the compound were combined and evaporated. Trituration with ether gave 0.4 g of crude product. This was dissolved in ethyl acetate and washed with water. The dried ethyl acetate solution was evaporated and purified by reversed phase chromatography in methanol water (80:20 vol/vol) to give 0.28 g of product m.p. 72°-75° C. (indefinite).

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 25 hours
  2. temperatureafter heating for 1 hour more
  3. extractionThe cooled aqueous mixture was extracted with chloroform
  4. customThe chloroform soluble material was chromatographed on a silica gel column
  5. additionThe fractions containing the compound
  6. customevaporated
  7. customTrituration with ether gave 0.4 g of crude product
  8. washwashed with water
  9. customThe dried ethyl acetate solution was evaporated
  10. custompurified by reversed phase chromatography in methanol water (80:20 vol/vol)

Sources & evidence

ORD record
ord-4a93a264a44643d6986ef7782ae9e6a2
Source dataset
uspto-grants-1981_11
Patent number
US04299823

Reaction notes

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