Triethylamine → (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine
Reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.Cl.[O:12]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13]1.C(N(CC)CC)C>CCO.O>[I:8][C:7]1[C:2]([NH:17][C@@H:14]2[CH2:15][CH2:16][O:12][CH2:13]2)=[N:3][C:4]([NH2:10])=[N:5][C:6]=1[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (7.03 g, 26.08 mmol), (R)-tetrahydrofuran-3-amine hydrochloride (Milestone PharmTech, 3.90 g, 31.3 mmol) and triethylamine (9.236 g, 91.3 mmol) in EtOH (150 mL) and water (50 mL) was refluxed for 2-3 days. The reaction was monitored by LC/MS. After completion, the reaction mixture was cooled to ambient temperature and partitioned between 150 mL of ethyl acetate and 200 mL of water. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate afforded (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (4.53 g, 54% yield). MS (EI) for C9H13IN4O: 321.0 (MH+).
Workup
- temperaturewas refluxed for 2-3 days
- custompartitioned between 150 mL of ethyl acetate and 200 mL of water
- extractionThe aqueous layer was extracted by ethyl acetate 3 times
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customRecrystallization of the residue from ethyl acetate
Sources & evidence
- ORD record
- ord-51c629c0ed884ffa986947f9f35853ef
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101622B2
Reaction notes
Loading…