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.NC1N=C(NCCCC)N=C2C=1NC(=O)N2CC1CCOC1.Cl.[OH-].[Na+]>CO.O1CCOCC1.O>[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
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To 2-[(2-cyclopropylethyl)oxy]-8-(methoxy)-9-[tetrahydro-3-furanylmethyl]-9H-purin-6-amine, Isomer 2 (1.45 g) in dry methanol (50 ml) at room temperature and under nitrogen, was added 4.0M hydrochloric acid in 1,4-dioxane (14 ml) in one go. The reaction was stirred at room temperature for 4 hours. The reaction was neutralised by the addition of 2M aqueous sodium hydroxide solution and concentrated in vacuo to yield an off white residue. This was taken up in water (40 ml) and filtered to afford a sand coloured solid. This was recrystallised from water:ethanol, 1:1 (75 ml) to afford a beige solid (765 mg).
Workup
- concentrationconcentrated in vacuo
- customto yield an off white residue
- filtrationfiltered
- customto afford a sand
- customThis was recrystallised from water
Sources & evidence
- ORD record
- ord-59118a64e63a4f7e82ba7d50f6e8129c
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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