Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([Cl:12])[N:6]=1)=[O:4].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1.O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:32][CH2:31][CH2:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[N:8]=[C:7]([Cl:12])[N:6]=1)=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 2,6-dichloro-pyrimidine-4-carboxylic acid methyl ester [1 g, 4.83 mmol, Intermediate (54)] and N,N-diisopropylethylamine (1.27 mL, 7.25 mmol) in THF (16 mL) is added 2-(4-methoxyphenyl)-ethylamine (707 μL, 4.83 mmol). The resulting mixture is stirred at ambient temperature for 20 hours and poured into 50 mL water and extracted three times with 40 mL ethyl acetate. The organic extracts are combined and washed with 20 mL brine, dried over magnesium sulfate, filtered and concentrated to afford a solid which is purified via flash column chromatography on silica gel (35 g) eluting with 5 to 50% EtOAc in heptane gradient to afford 2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [1 g, 64.5%, Intermediate (55)]. LCMS: RT=2.9 minutes, MS: 322 (M+H).
Workup
- extractionextracted three times with 40 mL ethyl acetate
- washwashed with 20 mL brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto afford a solid which
- customis purified via flash column chromatography on silica gel (35 g)
- washeluting with 5 to 50% EtOAc in heptane gradient
Sources & evidence
- ORD record
- ord-ad33d32ba9e9431db01186cb900e1cb8
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193183B2
Linked notes
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