Ammonia → 3-(6-Amino-2-propylthio-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

HRID 2255900Notes

Reaction equation

HRID 2255900 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH:14]2[CH2:18][CH:17]([CH2:19][OH:20])[CH:16]([OH:21])[CH:15]2[OH:22])=[N:4][C:5]([S:9][CH2:10][CH2:11][CH3:12])=[N:6][C:7]=1Cl.[NH3:23].[C:24](OC(OCC)OCC)(=O)C>>[NH2:23][C:7]1[N:6]=[C:5]([S:9][CH2:10][CH2:11][CH3:12])[N:4]=[C:3]2[C:2]=1[N:1]=[CH:24][N:13]2[CH:14]1[CH2:18][CH:17]([CH2:19][OH:20])[CH:16]([OH:21])[CH:15]1[OH:22]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 190286923-(5-Amino-6-chloro-2-propylthiopyrimidine-4-ylamino)-5-(hydroxymethyl)-cyclopentane-1,2-diol

Product 1

HCID 190286983-(6-Amino-2-propylthio-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol

Procedure

The product of step v) (0.2 g) and diethoxymethyl acetate (10 ml) were stirred at ambient temperature under nitrogen for 1 hour, then at 80° for 24 hours. Evaporation afforded a residue which was treated with liquid ammonia (15 ml) in an autoclave at 60° for 16 hours. The ammonia was allowed to evaporate and the residue taken up in 0.5M hydrochloric acid (10 ml) at 60° for 45 min. The volatiles were removed in vacuo and the remaining material dissolved in water (10 ml). Upon neutralisation with concentrated ammonia the sub-title compound crystallised and was collected and dried (0.15 g).

Workup

  1. customEvaporation
  2. customafforded a residue which
  3. customto evaporate
  4. waitthe residue taken up in 0.5M hydrochloric acid (10 ml) at 60° for 45 min
  5. customThe volatiles were removed in vacuo
  6. dissolutionthe remaining material dissolved in water (10 ml)
  7. customUpon neutralisation with concentrated ammonia the sub-title compound crystallised
  8. customwas collected
  9. customdried (0.15 g)

Sources & evidence

ORD record
ord-137e7fb100d64f3db92344887b5823c9
Source dataset
uspto-grants-1997_08
Patent number
US05654285

Reaction notes

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