Benzylamine → 4-N-benzyl-6-chloropyrimidine-2,4-diamine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.CCN(C(C)C)C(C)C.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O>CCO>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([NH:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 4,6-dichloro-2-pyrimidinamine (0.5 g, 3.1 mmol) in EtOH (10 mL) was added Hunig's base (1.1 mL, 6.1 mmol) followed by benzylamine (0.37 mL, 3.35 mmol) and the reaction mixture was stirred overnight at 100° C. The reaction mixture was poured onto water and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the crude title compound (670 mg) as a yellow solid. LC-MS (ES) m/z=235 [M+H]+.
Workup
- customThe organic layer was separated
- extractionthe aqueous layer was further extracted with EtOAc
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b9457f9a7b1c46bc8bd9e3da06095b79
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
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