Hydrochloric Acid → 6-Amino-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-3-furanylmethyl)-7,9-dihydro-8H-purin-8-one
Reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[C:12]([O:22]C)[N:13]3[CH2:16][CH:17]3[CH2:21][CH2:20][O:19][CH2:18]3)=[C:9]([NH2:24])[N:8]=2)[CH2:3][CH2:2]1.Cl.C(O)C.O>CO.O1CCOCC1>[NH2:24][C:9]1[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:22])[N:13]2[CH2:16][CH:17]1[CH2:21][CH2:20][O:19][CH2:18]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirring suspension of 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amine (814 mg) in methanol (3 ml) was added 4N HCl in dioxan (3 ml). After 3 h, the solvents were evaporated and the residue treated with water and neutralised by addition of saturated sodium bicarbonate with stirring. The resulting cream coloured solid was filtered off, washed with water and dried. The material was suspended in 1:1 ethanol:water (42 ml) but did not dissolve on boiling/stirring. Complete solution was obtained on adding a further 10 ml ethanol. More water (3 ml) was added and the clear solution allowed to cool to room temperature with stirring. The resulting cream coloured solid was filtered, washed with 1:1 ethanol:water (10 ml) and dried, yield 537 mg.
Workup
- customthe solvents were evaporated
- additionthe residue treated with water and neutralised by addition of saturated sodium bicarbonate
- filtrationwas filtered off
- washwashed with water
- customdried
- dissolutionwater (42 ml) but did not dissolve
- stirringon boiling/stirring
- customComplete solution was obtained
- stirringwith stirring
- filtrationwas filtered
- washwashed with 1:1 ethanol
- dry with materialwater (10 ml) and dried
Sources & evidence
- ORD record
- ord-073487356d23460ea60fafc42aa7bdc5
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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