Ammonia → 1-(6-amino-9H-purin-9-yl)-3-amino-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633301Notes

Reaction equation

HRID 1633301 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([C:7]([OH:9])=[O:8])[O:5][C@@H:4]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19]C(=O)C2C=CC=CC=2)[C@@H:3]1[OH:28].N>CO>[NH2:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:4]1[O:5][C@H:6]([C:7]([OH:9])=[O:8])[C@@H:2]([NH2:1])[C@H:3]1[OH:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 544839421-(6-amino-9H-purin-9-yl)-3-amino-1,3-dideoxy-beta-D-ribofuranuronic acidYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(6-benzoylamino-9H-purin-9-yl)-3-amino-1,3-dideoxy-β-D-ribofuranuronic acid (1.0 g) prepared in Example 1, concentrated aqueous ammonia (16 ml) and methanol (8 ml) was refluxed for 1.75 hours. The reaction mixture was evaporated to dryness and the residue was triturated in methanol (20 ml) to give 1-(6-amino-9H-purin-9-yl)-3-amino-1,3-dideoxy-β-D-ribofuranuronic acid (554 mg), mp. 245°-249° C. (dec.).

Workup

  1. temperaturewas refluxed for 1.75 hours
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was triturated in methanol (20 ml)

Sources & evidence

ORD record
ord-63ecc3d6428c4e059ee39a29b1b764fb
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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