2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine → 2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6-(1-pyrrolidinyl)-9H-purine

HRID 465727Notes

Reaction equation

HRID 465727 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[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4]([NH:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[N:3]=1>C(OCC)(=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[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([N:18]=[N+:19]=[N-:20])[CH2:12]2)=[C:4]([N:21]2[CH2:22][CH2:23][CH2:25][CH2:24]2)[N:3]=1

Participants

3

Reactant 1

HCID 867461752-amino-9-(3-azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine

Product 1

HCID 4764632-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6-(1-pyrrolidinyl)-9H-purineYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in a manner analogous to the preparation of 2-Amino-9-(3-azido-2,3-dideoxy-β-D-erythropentofuranosyl)-6-cyclopropylmethylamino-9H-purine (Example 15b). The reaction was worked up in an analogous manner except the combined ethyl acetate fractions were back washed with 150 mL of 1M potassium carbonate two times prior to chromatography. The product was isolated in 52% yield, 0.360 g, mp=180°-183°C.

Workup

  1. washwere back washed with 150 mL of 1M potassium carbonate two times
  2. customThe product was isolated in 52% yield, 0.360 g, mp=180°-183°C.

Sources & evidence

ORD record
ord-3ec15fc78587473b988a815ffeb97497
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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