Triethylamine → (1R,2S,3R,5R)-3-(6-amino-5-nitro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][C@@H:20]1[CH2:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]1[OH:28]>CN(C)C=O.O>[NH2:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH:19][C@@H:20]2[CH2:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]2[OH:28])[C:7]=1[N+:8]([O-:10])=[O:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 4-amino-6-chloro-5-nitropyrimidine (320 mg, 1.83 mmol) in N,N-dimethyl formamide (5 mL) and triethylamine (512 μL, 3.67 mmol) was added (1R,2S,3R,5R)-3-Amino-5-hydroxymethyl-cyclopentane-1,2-diol (293 mg, 2.02 mmol). The mixture was stirred at room temperature and monitored by thin layer chromatography until starting material was no longer detected. The reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (2×10 mL). The organic extract was washed with saturated aqueous sodium chloride (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was recrystallized from hot methanol/water to give a 298 mg of (1R,2S,3R,5R)-3-(6-amino-5-nitro-pyrimidin-4-ylamino)-5-hydroxymethyl-cyclopentane-1,2-diol as a yellow solid.
Workup
- extractionextracted with diethyl ether (2×10 mL)
- extractionThe organic extract
- washwas washed with saturated aqueous sodium chloride (20 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give the crude product
- customThe product was recrystallized from hot methanol/water
Sources & evidence
- ORD record
- ord-0d608112d56842a7a5667e890cd67e22
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291603B2
Reaction notes
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