Water → HCID 68849560, compound

HRID 2108345Notes

Reaction equation

HRID 2108345 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([O:32]CC)=[O:31])[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.O>[OH-].[K+].CO>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:25]1[CH:29]=[C:28]([C:30]([OH:32])=[O:31])[CH:27]=[N:26]1)=[N:14][C:15]=2[NH:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 962WaterHCID 68851187HCID 68851187, compound

Product 1

HCID 68849560HCID 68849560, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

40 mg of the ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazole-4-carboxylate prepared in Example 3 was dissolved in 2 mL of 1 N KOH in methanol. 200 mL of water was then added and the mixture stirred at at 50° C. for 24 hours. The solvent was then removed and the residue dissolved in 3 mL water and brought to a pH of 3-4 by addition of 37% HCl. The resulting solid was collected by filtration and washed with water and ether then air dried to provide the product, 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazole-4-carboxylic acid.

Workup

  1. customThe solvent was then removed
  2. dissolutionthe residue dissolved in 3 mL water
  3. additionbrought to a pH of 3-4 by addition of 37% HCl
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water and ether
  6. customair dried

Sources & evidence

ORD record
ord-460c74f06d0f4172baf3f3100c5e0380
Source dataset
uspto-grants-2009_04
Patent number
US07514417B2

Reaction notes

Loading…