Hydrochloric Acid → HCID 468292, compound

HRID 728665Notes

Reaction equation

HRID 728665 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[H-].[Na+].Cl>C(O)CCCC>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([O:17][CH2:16][CH2:14][CH2:13][CH2:12][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468292HCID 468292, compound

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of l±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544 g, 2 mmol) in 1-pentanol (10 mL) at 110° C. was added NaH (60% oil dispersion, 0.160g, 4 mmol). The mixture was stirred at 110° C. for 15 minutes, then cooled to room temperature. 1 N HCl was added to adjust the pH to 7.0, and the solvent was removed by evaporation. The residual oil was chromatographed on silica gel. Title compound was eluted with 7% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.481g, 76%); mp=139-141° C.;

Workup

  1. temperaturecooled to room temperature
  2. customthe solvent was removed by evaporation
  3. customThe residual oil was chromatographed on silica gel
  4. washTitle compound was eluted with 7% methanol-chloroform
  5. customwhite powder after crystallization from acetonitrile-methanol (0.481g, 76%)

Sources & evidence

ORD record
ord-63dd9abaf28445d79b151377f6548403
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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