Ammonia → Ethanol, 2-(6-amino-9H-purin-9-yl)methoxy-
Reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][O:12][CH2:13][CH2:14][O:15]C(=O)C1C=CC=CC=1.[NH3:24]>CO>[OH:15][CH2:14][CH2:13][O:12][CH2:11][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH2:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-chloro-9-(2-benzoyloxyethoxymethyl)purine (50g) and ammonia (31g) in methanol (120ml) was heated in a bomb at 95° C. for 18 hours. The reaction mixture was removed from the bomb and the solvent evaporated under reduced pressure at 50° C. The resulting solid was triturated first with water and then, after drying, with chloroform. The solid, 9-(2-hydroxyethoxymethyl)adenine, was retained, and the aqueous triturate was extracted several times with chloroform. The aqueous extracts were treated with a strongly basic ion exchange resin and then evaporated to dryness under reduced pressure. The remaining solid was combined with that from the trituration step and recrystallized from isopropanol to give 22g (70% of theoretical) of white 9-(2-hydroxyethoxymethyl)adenine, m.p. 199.5°-200° C.
Workup
- customThe reaction mixture was removed from the bomb
- customthe solvent evaporated under reduced pressure at 50° C
- customThe resulting solid was triturated first with water
- dry with materialafter drying, with chloroform
- customthe aqueous triturate
- extractionwas extracted several times with chloroform
- additionThe aqueous extracts were treated with a strongly basic ion exchange resin
- customevaporated to dryness under reduced pressure
- customrecrystallized from isopropanol
Sources & evidence
- ORD record
- ord-b2ca07de623a485ca729e595faf7385c
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04199574
Reaction notes
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