Sodium Hydroxide → Abacavir

HRID 1417009Notes

Reaction equation

HRID 1417009 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.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[OH-].[Na+]>C(O)C>[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]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 441300AbacavirYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1S,4R)-4-(2-Amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol (U.S. Pat. No. 5,206,435) or the hydrochloride salt thereof (Example 8) was refluxed in ethanol with 10 molar equivalents of cyclopropylamine for 2 hours. The resulting solution was cooled to ambient temperature and 1 N sodium hydroxide (1 or 2 molar equivalents, depending on whether the starting material was VIIa or the hydrochloride salt of VIIa) was added. The volatiles were evaporated in vacuo. (1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol (IXa) was washed from a silica gel pad eluted with 5% methanol-chloroform or 10% methanol-ethyl acetate and isolated as a white solid foam (80%); spectra identical to those of the product of Example 9.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. wash(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol (IXa) was washed from a silica gel pad
  3. washeluted with 5% methanol-chloroform or 10% methanol-ethyl acetate

Sources & evidence

ORD record
ord-4399063af63d4603bf634064b84f49c9
Source dataset
uspto-grants-1999_06
Patent number
US05917041

Reaction notes

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