Sodium Hydroxide → 118353-05-2
Reaction equation
CO[C:3](=[O:5])O.[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[CH2:20][C@@H:19]([CH2:21][OH:22])[CH:18]=[CH:17]2)=C(Cl)[N:8]=1.[OH-].[Na+]>O>[NH2:6][C:7]1[NH:8][C:3](=[O:5])[C:10]2[N:11]=[CH:12][N:13]([C@H:16]3[CH2:20][C@@H:19]([CH2:21][OH:22])[CH:18]=[CH:17]3)[C:14]=2[N:15]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a 5 mL round-bottom flask equipped with a reflux condenser is added cis-2-amino-6-chloro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purine methylcarbonate as prepared in Example 3 (10 mg, 0.03I mmol), sodium hydroxide (2.5 mg, 0.062 mmol), and deionized water (1 mL). The resultant heterogeneous mixture is heated at 75° C. for 12 hours. The reaction mixture becomes a pale amber solution which is filtered hot through a bed of diatomaceous earth. The pH of the filtrate is adjusted to pH 7 with 1N hydrochloric acid. Acetonitrile is added and the solution is concentrated in vacuo to a solid via azeotropic removal of water. The solid is tritriated with 2 mL of methanol and the solution is filtered. The filtrate is concentrated in vacuo to give cis-2-amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl ]-6H-purine-6-one as a white solid which exhibits the following physical data: IR (nujol mull, cm-1) 3500- 3600 (br, m), 1725 (m), 1630 (s), 1605 (s); UV (EtOH, nm) λmax=275, 255; λmin=225; and mp 268-270° C.
Workup
- customTo a 5 mL round-bottom flask equipped with a reflux condenser
- filtrationis filtered hot through a bed of diatomaceous earth
- additionAcetonitrile is added
- concentrationthe solution is concentrated in vacuo to a solid via azeotropic removal of water
- filtrationthe solution is filtered
- concentrationThe filtrate is concentrated in vacuo
Sources & evidence
- ORD record
- ord-f089a28a34bf483bb14b7e5d6d29b24c
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05126452
Reaction notes
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